id	sid	tid	token	lemma	pos
eurjchem-503	1	1	untitled	untitle	VERB
eurjchem-503	1	2	european	european	PROPN
eurjchem-503	1	3	journal	journal	PROPN
eurjchem-503	1	4	of	of	ADP
eurjchem-503	1	5	chemistry	chemistry	NOUN
eurjchem-503	1	6	3	3	NUM
eurjchem-503	1	7	(	(	PUNCT
eurjchem-503	1	8	1	1	NUM
eurjchem-503	1	9	)	)	PUNCT
eurjchem-503	1	10	(	(	PUNCT
eurjchem-503	1	11	2012	2012	NUM
eurjchem-503	1	12	)	)	PUNCT
eurjchem-503	1	13	26‐31	26‐31	NUM
eurjchem-503	1	14	european	european	ADJ
eurjchem-503	1	15	journal	journal	PROPN
eurjchem-503	1	16	of	of	ADP
eurjchem-503	1	17	chemistry	chemistry	NOUN
eurjchem-503	1	18	issn	issn	PROPN
eurjchem-503	1	19	2153‐2249	2153‐2249	PROPN
eurjchem-503	1	20	(	(	PUNCT
eurjchem-503	1	21	print	print	NOUN
eurjchem-503	1	22	)	)	PUNCT
eurjchem-503	1	23	/	/	SYM
eurjchem-503	1	24	issn	issn	PROPN
eurjchem-503	1	25	2153‐2257	2153‐2257	NUM
eurjchem-503	1	26	(	(	PUNCT
eurjchem-503	1	27	online	online	ADJ
eurjchem-503	1	28	)	)	PUNCT
eurjchem-503	1	29			NOUN
eurjchem-503	1	30	2012	2012	NUM
eurjchem-503	1	31	eurjchem	eurjchem	PROPN
eurjchem-503	1	32	doi:10.5155	doi:10.5155	PROPN
eurjchem-503	1	33	/	/	SYM
eurjchem-503	1	34	eurjchem.3.1.26‐31.503	eurjchem.3.1.26‐31.503	PROPN
eurjchem-503	1	35	european	european	PROPN
eurjchem-503	1	36	journal	journal	PROPN
eurjchem-503	1	37	of	of	ADP
eurjchem-503	1	38	chemistry	chemistry	PROPN
eurjchem-503	1	39	journal	journal	PROPN
eurjchem-503	1	40	homepage	homepage	NOUN
eurjchem-503	1	41	:	:	PUNCT
eurjchem-503	1	42	www.eurjchem.com	www.eurjchem.com	X
eurjchem-503	1	43	studies	study	NOUN
eurjchem-503	1	44	towards	towards	ADP
eurjchem-503	1	45	the	the	DET
eurjchem-503	1	46	synthesis	synthesis	NOUN
eurjchem-503	1	47	of	of	ADP
eurjchem-503	1	48	(	(	PUNCT
eurjchem-503	1	49	±)‐reserpine	±)‐reserpine	NUM
eurjchem-503	1	50	:	:	PUNCT
eurjchem-503	1	51	photocyclization	photocyclization	NOUN
eurjchem-503	1	52	mediated	mediate	VERB
eurjchem-503	1	53	a	a	DET
eurjchem-503	1	54	novel	novel	ADJ
eurjchem-503	1	55	and	and	CCONJ
eurjchem-503	1	56	efficient	efficient	ADJ
eurjchem-503	1	57	synthesis	synthesis	NOUN
eurjchem-503	1	58	of	of	ADP
eurjchem-503	1	59	11,18‐dimethoxy‐(20α)‐18,19‐didehydro‐	11,18‐dimethoxy‐(20α)‐18,19‐didehydro‐	NUM
eurjchem-503	1	60	yohimban‐17‐one	yohimban‐17‐one	NOUN
eurjchem-503	1	61	muhammad	muhammad	PROPN
eurjchem-503	1	62	yara	yara	PROPN
eurjchem-503	1	63	,	,	PUNCT
eurjchem-503	1	64	*	*	PROPN
eurjchem-503	1	65	,	,	PUNCT
eurjchem-503	1	66	muhammad	muhammad	PROPN
eurjchem-503	1	67	arshadb	arshadb	PROPN
eurjchem-503	1	68	,	,	PUNCT
eurjchem-503	1	69	muhammad	muhammad	PROPN
eurjchem-503	1	70	nadeem	nadeem	PROPN
eurjchem-503	1	71	akhtarc	akhtarc	PROPN
eurjchem-503	1	72	,	,	PUNCT
eurjchem-503	1	73	sohail	sohail	PROPN
eurjchem-503	1	74	anjum	anjum	PROPN
eurjchem-503	1	75	shahzadd	shahzadd	PROPN
eurjchem-503	1	76	,	,	PUNCT
eurjchem-503	1	77	islam	islam	PROPN
eurjchem-503	1	78	ullah	ullah	PROPN
eurjchem-503	1	79	khand	khand	PROPN
eurjchem-503	1	80	,	,	PUNCT
eurjchem-503	1	81	zulfiqar	zulfiqar	PROPN
eurjchem-503	1	82	ali	ali	PROPN
eurjchem-503	1	83	khane	khane	PROPN
eurjchem-503	1	84	,	,	PUNCT
eurjchem-503	1	85	nisar	nisar	PROPN
eurjchem-503	1	86	ullahf	ullahf	PROPN
eurjchem-503	1	87	and	and	CCONJ
eurjchem-503	1	88	ichiya	ichiya	PROPN
eurjchem-503	1	89	ninomiyag	ninomiyag	VERB
eurjchem-503	1	90	a	a	DET
eurjchem-503	1	91	interdisciplinary	interdisciplinary	ADJ
eurjchem-503	1	92	research	research	NOUN
eurjchem-503	1	93	center	center	NOUN
eurjchem-503	1	94	in	in	ADP
eurjchem-503	1	95	biomedical	biomedical	ADJ
eurjchem-503	1	96	materials	material	NOUN
eurjchem-503	1	97	,	,	PUNCT
eurjchem-503	1	98	comsats	comsats	PROPN
eurjchem-503	1	99	institute	institute	PROPN
eurjchem-503	1	100	of	of	ADP
eurjchem-503	1	101	information	information	NOUN
eurjchem-503	1	102	technology	technology	NOUN
eurjchem-503	1	103	,	,	PUNCT
eurjchem-503	1	104	lahore	lahore	NOUN
eurjchem-503	1	105	,	,	PUNCT
eurjchem-503	1	106	54000	54000	NUM
eurjchem-503	1	107	,	,	PUNCT
eurjchem-503	1	108	pakistan	pakistan	PROPN
eurjchem-503	1	109	b	b	PROPN
eurjchem-503	1	110	institute	institute	PROPN
eurjchem-503	1	111	of	of	ADP
eurjchem-503	1	112	chemistry	chemistry	NOUN
eurjchem-503	1	113	,	,	PUNCT
eurjchem-503	1	114	university	university	NOUN
eurjchem-503	1	115	of	of	ADP
eurjchem-503	1	116	the	the	DET
eurjchem-503	1	117	punjab	punjab	ADJ
eurjchem-503	1	118	,	,	PUNCT
eurjchem-503	1	119	lahore	lahore	NOUN
eurjchem-503	1	120	,	,	PUNCT
eurjchem-503	1	121	54590	54590	NUM
eurjchem-503	1	122	,	,	PUNCT
eurjchem-503	1	123	pakistan	pakistan	PROPN
eurjchem-503	1	124	c	c	PROPN
eurjchem-503	1	125	laboratory	laboratory	NOUN
eurjchem-503	1	126	of	of	ADP
eurjchem-503	1	127	natural	natural	ADJ
eurjchem-503	1	128	products	product	NOUN
eurjchem-503	1	129	,	,	PUNCT
eurjchem-503	1	130	institute	institute	NOUN
eurjchem-503	1	131	of	of	ADP
eurjchem-503	1	132	bioscience	bioscience	PROPN
eurjchem-503	1	133	,	,	PUNCT
eurjchem-503	1	134	university	university	NOUN
eurjchem-503	1	135	putra	putra	PROPN
eurjchem-503	1	136	malaysia	malaysia	PROPN
eurjchem-503	1	137	,	,	PUNCT
eurjchem-503	1	138	serdang	serdang	PROPN
eurjchem-503	1	139	,	,	PUNCT
eurjchem-503	1	140	selangor	selangor	PROPN
eurjchem-503	1	141	darul	darul	PROPN
eurjchem-503	1	142	ehsan	ehsan	PROPN
eurjchem-503	1	143	,	,	PUNCT
eurjchem-503	1	144	43400	43400	NUM
eurjchem-503	1	145	,	,	PUNCT
eurjchem-503	1	146	malaysia	malaysia	PROPN
eurjchem-503	1	147	d	d	PROPN
eurjchem-503	1	148	department	department	NOUN
eurjchem-503	1	149	of	of	ADP
eurjchem-503	1	150	chemistry	chemistry	NOUN
eurjchem-503	1	151	,	,	PUNCT
eurjchem-503	1	152	government	government	NOUN
eurjchem-503	1	153	college	college	NOUN
eurjchem-503	1	154	university	university	PROPN
eurjchem-503	1	155	,	,	PUNCT
eurjchem-503	1	156	lahore	lahore	NOUN
eurjchem-503	1	157	,	,	PUNCT
eurjchem-503	1	158	54000	54000	NUM
eurjchem-503	1	159	,	,	PUNCT
eurjchem-503	1	160	pakistan	pakistan	PROPN
eurjchem-503	1	161	e	e	PROPN
eurjchem-503	1	162	department	department	PROPN
eurjchem-503	1	163	of	of	ADP
eurjchem-503	1	164	chemistry	chemistry	NOUN
eurjchem-503	1	165	,	,	PUNCT
eurjchem-503	1	166	government	government	NOUN
eurjchem-503	1	167	college	college	PROPN
eurjchem-503	1	168	university	university	PROPN
eurjchem-503	1	169	,	,	PUNCT
eurjchem-503	1	170	faisalabad	faisalabad	PROPN
eurjchem-503	1	171	,	,	PUNCT
eurjchem-503	1	172	38000	38000	NUM
eurjchem-503	1	173	,	,	PUNCT
eurjchem-503	1	174	pakistan	pakistan	PROPN
eurjchem-503	1	175	f	f	PROPN
eurjchem-503	1	176	department	department	PROPN
eurjchem-503	1	177	of	of	ADP
eurjchem-503	1	178	chemistry	chemistry	NOUN
eurjchem-503	1	179	,	,	PUNCT
eurjchem-503	1	180	king	king	PROPN
eurjchem-503	1	181	fahd	fahd	PROPN
eurjchem-503	1	182	university	university	PROPN
eurjchem-503	1	183	of	of	ADP
eurjchem-503	1	184	petroleum	petroleum	NOUN
eurjchem-503	1	185	and	and	CCONJ
eurjchem-503	1	186	minerals	mineral	NOUN
eurjchem-503	1	187	,	,	PUNCT
eurjchem-503	1	188	dhahran	dhahran	NOUN
eurjchem-503	1	189	,	,	PUNCT
eurjchem-503	1	190	31261	31261	NUM
eurjchem-503	1	191	,	,	PUNCT
eurjchem-503	1	192	saudi	saudi	PROPN
eurjchem-503	1	193	arabia	arabia	PROPN
eurjchem-503	1	194	g	g	PROPN
eurjchem-503	1	195	international	international	ADJ
eurjchem-503	1	196	center	center	NOUN
eurjchem-503	1	197	for	for	ADP
eurjchem-503	1	198	chemical	chemical	NOUN
eurjchem-503	1	199	and	and	CCONJ
eurjchem-503	1	200	biological	biological	ADJ
eurjchem-503	1	201	sciences	science	NOUN
eurjchem-503	1	202	,	,	PUNCT
eurjchem-503	1	203	hussain	hussain	PROPN
eurjchem-503	1	204	ibrahim	ibrahim	PROPN
eurjchem-503	1	205	jamal	jamal	PROPN
eurjchem-503	1	206	research	research	PROPN
eurjchem-503	1	207	institute	institute	PROPN
eurjchem-503	1	208	of	of	ADP
eurjchem-503	1	209	chemistry	chemistry	PROPN
eurjchem-503	1	210	,	,	PUNCT
eurjchem-503	1	211	university	university	PROPN
eurjchem-503	1	212	of	of	ADP
eurjchem-503	1	213	karachi	karachi	PROPN
eurjchem-503	1	214	,	,	PUNCT
eurjchem-503	1	215	karachi	karachi	PROPN
eurjchem-503	1	216	,	,	PUNCT
eurjchem-503	1	217	75270	75270	NUM
eurjchem-503	1	218	,	,	PUNCT
eurjchem-503	1	219	pakistan	pakistan	PROPN
eurjchem-503	1	220	*	*	PUNCT
eurjchem-503	1	221	corresponding	correspond	VERB
eurjchem-503	1	222	author	author	NOUN
eurjchem-503	1	223	at	at	ADP
eurjchem-503	1	224	:	:	PUNCT
eurjchem-503	1	225	interdisciplinary	interdisciplinary	ADJ
eurjchem-503	1	226	research	research	NOUN
eurjchem-503	1	227	center	center	NOUN
eurjchem-503	1	228	in	in	ADP
eurjchem-503	1	229	biomedical	biomedical	ADJ
eurjchem-503	1	230	materials	material	NOUN
eurjchem-503	1	231	,	,	PUNCT
eurjchem-503	1	232	comsats	comsats	PROPN
eurjchem-503	1	233	institute	institute	PROPN
eurjchem-503	1	234	of	of	ADP
eurjchem-503	1	235	information	information	NOUN
eurjchem-503	1	236	technology	technology	NOUN
eurjchem-503	1	237	,	,	PUNCT
eurjchem-503	1	238	lahore	lahore	NOUN
eurjchem-503	1	239	,	,	PUNCT
eurjchem-503	1	240	54000	54000	NUM
eurjchem-503	1	241	,	,	PUNCT
eurjchem-503	1	242	pakistan	pakistan	PROPN
eurjchem-503	1	243	.	.	PUNCT
eurjchem-503	2	1	tel	tel	PROPN
eurjchem-503	2	2	.	.	PUNCT
eurjchem-503	2	3	:	:	PUNCT
eurjchem-503	3	1	+92.42.111001007	+92.42.111001007	NUM
eurjchem-503	3	2	;	;	PUNCT
eurjchem-503	3	3	fax	fax	NOUN
eurjchem-503	3	4	:	:	PUNCT
eurjchem-503	3	5	+92.42.5321090	+92.42.5321090	NUM
eurjchem-503	3	6	.	.	PUNCT
eurjchem-503	3	7	e‐mail	e‐mail	PUNCT
eurjchem-503	4	1	address	address	NOUN
eurjchem-503	4	2	:	:	PUNCT
eurjchem-503	4	3	myar1980@yahoo.com	myar1980@yahoo.com	X
eurjchem-503	4	4	(	(	PUNCT
eurjchem-503	4	5	m.	m.	PROPN
eurjchem-503	4	6	yar	yar	PROPN
eurjchem-503	4	7	)	)	PUNCT
eurjchem-503	4	8	.	.	PUNCT
eurjchem-503	5	1	article	article	NOUN
eurjchem-503	5	2	information	information	PROPN
eurjchem-503	5	3	abstract	abstract	ADV
eurjchem-503	5	4	received	receive	VERB
eurjchem-503	5	5	:	:	PUNCT
eurjchem-503	5	6	08	08	NUM
eurjchem-503	5	7	august	august	PROPN
eurjchem-503	5	8	2011	2011	NUM
eurjchem-503	5	9	received	receive	VERB
eurjchem-503	5	10	in	in	ADP
eurjchem-503	5	11	revised	revise	VERB
eurjchem-503	5	12	form	form	NOUN
eurjchem-503	5	13	:	:	PUNCT
eurjchem-503	5	14	06	06	NUM
eurjchem-503	5	15	october	october	PROPN
eurjchem-503	5	16	2011	2011	NUM
eurjchem-503	5	17	accepted	accept	VERB
eurjchem-503	5	18	:	:	PUNCT
eurjchem-503	5	19	24	24	NUM
eurjchem-503	5	20	october	october	PROPN
eurjchem-503	5	21	2011	2011	NUM
eurjchem-503	5	22	online	online	NOUN
eurjchem-503	5	23	:	:	PUNCT
eurjchem-503	5	24	31	31	NUM
eurjchem-503	5	25	march	march	NOUN
eurjchem-503	5	26	2012	2012	NUM
eurjchem-503	5	27	keywords	keyword	VERB
eurjchem-503	5	28	a	a	DET
eurjchem-503	5	29	short	short	ADJ
eurjchem-503	5	30	,	,	PUNCT
eurjchem-503	5	31	highly	highly	ADV
eurjchem-503	5	32	efficient	efficient	ADJ
eurjchem-503	5	33	synthesis	synthesis	NOUN
eurjchem-503	5	34	of	of	ADP
eurjchem-503	5	35	advanced	advanced	ADJ
eurjchem-503	5	36	intermediates	intermediate	NOUN
eurjchem-503	5	37	to	to	PART
eurjchem-503	5	38	reserpine	reserpine	VERB
eurjchem-503	5	39	1	1	NUM
eurjchem-503	5	40	has	have	AUX
eurjchem-503	5	41	been	be	AUX
eurjchem-503	5	42	developed	develop	VERB
eurjchem-503	5	43	starting	start	VERB
eurjchem-503	5	44	from	from	ADP
eurjchem-503	5	45	enamide	enamide	ADJ
eurjchem-503	5	46	8	8	NUM
eurjchem-503	5	47	.	.	PUNCT
eurjchem-503	6	1	the	the	DET
eurjchem-503	6	2	enamide	enamide	ADJ
eurjchem-503	6	3	underwent	underwent	NOUN
eurjchem-503	6	4	photocyclization	photocyclization	NOUN
eurjchem-503	6	5	reaction	reaction	NOUN
eurjchem-503	6	6	using	use	VERB
eurjchem-503	6	7	high	high	ADJ
eurjchem-503	6	8	pressure	pressure	NOUN
eurjchem-503	6	9	mercury	mercury	NOUN
eurjchem-503	6	10	lamp	lamp	NOUN
eurjchem-503	6	11	to	to	PART
eurjchem-503	6	12	afford	afford	VERB
eurjchem-503	6	13	the	the	DET
eurjchem-503	6	14	lactam	lactam	NOUN
eurjchem-503	6	15	9	9	NUM
eurjchem-503	6	16	in	in	ADP
eurjchem-503	6	17	excellent	excellent	ADJ
eurjchem-503	6	18	yield	yield	NOUN
eurjchem-503	6	19	.	.	PUNCT
eurjchem-503	7	1	then	then	ADV
eurjchem-503	7	2	lactam	lactam	NOUN
eurjchem-503	7	3	was	be	AUX
eurjchem-503	7	4	reduced	reduce	VERB
eurjchem-503	7	5	to	to	ADP
eurjchem-503	7	6	the	the	DET
eurjchem-503	7	7	required	require	VERB
eurjchem-503	7	8	amine	amine	ADJ
eurjchem-503	7	9	10	10	NUM
eurjchem-503	7	10	,	,	PUNCT
eurjchem-503	7	11	which	which	PRON
eurjchem-503	7	12	upon	upon	SCONJ
eurjchem-503	7	13	acidic	acidic	ADJ
eurjchem-503	7	14	hydrolysis	hydrolysis	NOUN
eurjchem-503	7	15	gave	give	VERB
eurjchem-503	7	16	the	the	DET
eurjchem-503	7	17	nonconjugate	nonconjugate	ADJ
eurjchem-503	7	18	ketone	ketone	NOUN
eurjchem-503	7	19	product	product	NOUN
eurjchem-503	7	20	11	11	NUM
eurjchem-503	7	21	,	,	PUNCT
eurjchem-503	7	22	followed	follow	VERB
eurjchem-503	7	23	by	by	ADP
eurjchem-503	7	24	reaction	reaction	NOUN
eurjchem-503	7	25	with	with	ADP
eurjchem-503	7	26	sodium	sodium	NOUN
eurjchem-503	7	27	hydroxide	hydroxide	NOUN
eurjchem-503	7	28	resulted	result	VERB
eurjchem-503	7	29	the	the	DET
eurjchem-503	7	30	desired	desire	VERB
eurjchem-503	7	31	conjugate	conjugate	ADJ
eurjchem-503	7	32	ketone	ketone	NOUN
eurjchem-503	7	33	12	12	NUM
eurjchem-503	7	34	.	.	PUNCT
eurjchem-503	7	35	epoxidation	epoxidation	NOUN
eurjchem-503	7	36	,	,	PUNCT
eurjchem-503	7	37	and	and	CCONJ
eurjchem-503	7	38	then	then	ADV
eurjchem-503	7	39	ring	ring	VERB
eurjchem-503	7	40	opening	opening	NOUN
eurjchem-503	7	41	of	of	ADP
eurjchem-503	7	42	the	the	DET
eurjchem-503	7	43	epoxide	epoxide	NOUN
eurjchem-503	7	44	13	13	NUM
eurjchem-503	7	45	with	with	ADP
eurjchem-503	7	46	methanol	methanol	NOUN
eurjchem-503	7	47	yielded	yield	VERB
eurjchem-503	7	48	the	the	DET
eurjchem-503	7	49	desired	desire	VERB
eurjchem-503	7	50	product	product	NOUN
eurjchem-503	7	51	14	14	NUM
eurjchem-503	7	52	,	,	PUNCT
eurjchem-503	7	53	which	which	PRON
eurjchem-503	7	54	is	be	AUX
eurjchem-503	7	55	key	key	ADJ
eurjchem-503	7	56	intermediate	intermediate	ADJ
eurjchem-503	7	57	to	to	ADP
eurjchem-503	7	58	the	the	DET
eurjchem-503	7	59	total	total	ADJ
eurjchem-503	7	60	synthesis	synthesis	NOUN
eurjchem-503	7	61	of	of	ADP
eurjchem-503	7	62	(	(	PUNCT
eurjchem-503	7	63	±)‐reserpine	±)‐reserpine	X
eurjchem-503	7	64	.	.	PUNCT
eurjchem-503	8	1	lactam	lactam	NOUN
eurjchem-503	8	2	reserpine	reserpine	NOUN
eurjchem-503	8	3	harmaline	harmaline	PROPN
eurjchem-503	8	4	total	total	ADJ
eurjchem-503	8	5	synthesis	synthesis	NOUN
eurjchem-503	8	6	enamide	enamide	VERB
eurjchem-503	8	7	photocyclization	photocyclization	NOUN
eurjchem-503	8	8	hypertension	hypertension	NOUN
eurjchem-503	8	9	and	and	CCONJ
eurjchem-503	8	10	mental	mental	ADJ
eurjchem-503	8	11	disorders	disorder	NOUN
eurjchem-503	8	12	1	1	NUM
eurjchem-503	8	13	.	.	PUNCT
eurjchem-503	8	14	introduction	introduction	NOUN
eurjchem-503	8	15	reserpine	reserpine	NOUN
eurjchem-503	8	16	1	1	NUM
eurjchem-503	8	17	,	,	PUNCT
eurjchem-503	8	18	a	a	DET
eurjchem-503	8	19	naturally	naturally	ADV
eurjchem-503	8	20	occurring	occur	VERB
eurjchem-503	8	21	alkaloid	alkaloid	PROPN
eurjchem-503	8	22	was	be	AUX
eurjchem-503	8	23	initially	initially	ADV
eurjchem-503	8	24	isolated	isolate	VERB
eurjchem-503	8	25	from	from	ADP
eurjchem-503	8	26	rauwolfia	rauwolfia	NOUN
eurjchem-503	8	27	serpentina	serpentina	NOUN
eurjchem-503	8	28	[	[	X
eurjchem-503	8	29	1	1	NUM
eurjchem-503	8	30	]	]	PUNCT
eurjchem-503	8	31	,	,	PUNCT
eurjchem-503	8	32	and	and	CCONJ
eurjchem-503	8	33	is	be	AUX
eurjchem-503	8	34	regarded	regard	VERB
eurjchem-503	8	35	one	one	NUM
eurjchem-503	8	36	of	of	ADP
eurjchem-503	8	37	the	the	DET
eurjchem-503	8	38	most	most	ADV
eurjchem-503	8	39	important	important	ADJ
eurjchem-503	8	40	medicinal	medicinal	ADJ
eurjchem-503	8	41	agents	agent	NOUN
eurjchem-503	8	42	existing	exist	VERB
eurjchem-503	8	43	in	in	ADP
eurjchem-503	8	44	nature	nature	NOUN
eurjchem-503	8	45	mainly	mainly	ADV
eurjchem-503	8	46	due	due	ADP
eurjchem-503	8	47	to	to	ADP
eurjchem-503	8	48	its	its	PRON
eurjchem-503	8	49	extensive	extensive	ADJ
eurjchem-503	8	50	use	use	NOUN
eurjchem-503	8	51	in	in	ADP
eurjchem-503	8	52	the	the	DET
eurjchem-503	8	53	treatment	treatment	NOUN
eurjchem-503	8	54	of	of	ADP
eurjchem-503	8	55	hypertension	hypertension	NOUN
eurjchem-503	8	56	and	and	CCONJ
eurjchem-503	8	57	mental	mental	ADJ
eurjchem-503	8	58	disorder	disorder	NOUN
eurjchem-503	8	59	[	[	X
eurjchem-503	8	60	2‐5	2‐5	NOUN
eurjchem-503	8	61	]	]	PUNCT
eurjchem-503	8	62	.	.	PUNCT
eurjchem-503	9	1	reserpine	reserpine	NOUN
eurjchem-503	9	2	is	be	AUX
eurjchem-503	9	3	one	one	NUM
eurjchem-503	9	4	of	of	ADP
eurjchem-503	9	5	the	the	DET
eurjchem-503	9	6	most	most	ADV
eurjchem-503	9	7	complex	complex	ADJ
eurjchem-503	9	8	natural	natural	ADJ
eurjchem-503	9	9	products	product	NOUN
eurjchem-503	9	10	[	[	X
eurjchem-503	9	11	6‐9	6‐9	NOUN
eurjchem-503	9	12	]	]	PUNCT
eurjchem-503	9	13	,	,	PUNCT
eurjchem-503	9	14	having	have	VERB
eurjchem-503	9	15	six	six	NUM
eurjchem-503	9	16	chiral	chiral	ADJ
eurjchem-503	9	17	centers	center	NOUN
eurjchem-503	9	18	and	and	CCONJ
eurjchem-503	9	19	a	a	DET
eurjchem-503	9	20	pentacyclic	pentacyclic	ADJ
eurjchem-503	9	21	motif	motif	NOUN
eurjchem-503	9	22	(	(	PUNCT
eurjchem-503	9	23	figure	figure	NOUN
eurjchem-503	9	24	1	1	NUM
eurjchem-503	9	25	)	)	PUNCT
eurjchem-503	10	1	[	[	X
eurjchem-503	10	2	10‐19	10‐19	NUM
eurjchem-503	10	3	]	]	X
eurjchem-503	10	4	.	.	PUNCT
eurjchem-503	11	1	the	the	DET
eurjchem-503	11	2	chemical	chemical	ADJ
eurjchem-503	11	3	and	and	CCONJ
eurjchem-503	11	4	pharmacological	pharmacological	ADJ
eurjchem-503	11	5	properties	property	NOUN
eurjchem-503	11	6	of	of	ADP
eurjchem-503	11	7	reserpine	reserpine	NOUN
eurjchem-503	11	8	have	have	AUX
eurjchem-503	11	9	made	make	VERB
eurjchem-503	11	10	it	it	PRON
eurjchem-503	11	11	an	an	DET
eurjchem-503	11	12	interesting	interesting	ADJ
eurjchem-503	11	13	and	and	CCONJ
eurjchem-503	11	14	challenging	challenging	ADJ
eurjchem-503	11	15	target	target	NOUN
eurjchem-503	11	16	for	for	ADP
eurjchem-503	11	17	synthesis	synthesis	NOUN
eurjchem-503	11	18	.	.	PUNCT
eurjchem-503	12	1	the	the	DET
eurjchem-503	12	2	first	first	ADJ
eurjchem-503	12	3	total	total	ADJ
eurjchem-503	12	4	synthesis	synthesis	NOUN
eurjchem-503	12	5	of	of	ADP
eurjchem-503	12	6	reserpine	reserpine	NOUN
eurjchem-503	12	7	was	be	AUX
eurjchem-503	12	8	accomplished	accomplish	VERB
eurjchem-503	12	9	by	by	ADP
eurjchem-503	12	10	woodward	woodward	NOUN
eurjchem-503	12	11	and	and	CCONJ
eurjchem-503	12	12	co‐workers	co‐worker	NOUN
eurjchem-503	12	13	in	in	ADP
eurjchem-503	12	14	1956	1956	NUM
eurjchem-503	12	15	,	,	PUNCT
eurjchem-503	12	16	and	and	CCONJ
eurjchem-503	12	17	is	be	AUX
eurjchem-503	12	18	considered	consider	VERB
eurjchem-503	12	19	a	a	DET
eurjchem-503	12	20	milestone	milestone	NOUN
eurjchem-503	12	21	in	in	ADP
eurjchem-503	12	22	the	the	DET
eurjchem-503	12	23	field	field	NOUN
eurjchem-503	12	24	of	of	ADP
eurjchem-503	12	25	organic	organic	ADJ
eurjchem-503	12	26	synthesis	synthesis	NOUN
eurjchem-503	12	27	[	[	X
eurjchem-503	12	28	10,11,20	10,11,20	NUM
eurjchem-503	12	29	]	]	PUNCT
eurjchem-503	12	30	.	.	PUNCT
eurjchem-503	13	1	woodward	woodward	NOUN
eurjchem-503	13	2	and	and	CCONJ
eurjchem-503	13	3	co‐workers	co‐worker	NOUN
eurjchem-503	13	4	used	use	VERB
eurjchem-503	13	5	the	the	DET
eurjchem-503	13	6	diels‐alder	diels‐alder	NOUN
eurjchem-503	13	7	reaction	reaction	NOUN
eurjchem-503	13	8	to	to	PART
eurjchem-503	13	9	generate	generate	VERB
eurjchem-503	13	10	the	the	DET
eurjchem-503	13	11	rings	ring	NOUN
eurjchem-503	13	12	d	d	NOUN
eurjchem-503	13	13	and	and	CCONJ
eurjchem-503	13	14	e	e	PROPN
eurjchem-503	13	15	starting	start	VERB
eurjchem-503	13	16	from	from	ADP
eurjchem-503	13	17	vinyl	vinyl	NOUN
eurjchem-503	13	18	acrylic	acrylic	NOUN
eurjchem-503	13	19	acid	acid	NOUN
eurjchem-503	13	20	and	and	CCONJ
eurjchem-503	13	21	quinone	quinone	NOUN
eurjchem-503	13	22	[	[	X
eurjchem-503	13	23	10	10	NUM
eurjchem-503	13	24	]	]	PUNCT
eurjchem-503	13	25	.	.	PUNCT
eurjchem-503	14	1	following	follow	VERB
eurjchem-503	14	2	woodward	woodward	PROPN
eurjchem-503	14	3	considerable	considerable	ADJ
eurjchem-503	14	4	attention	attention	NOUN
eurjchem-503	14	5	has	have	AUX
eurjchem-503	14	6	been	be	AUX
eurjchem-503	14	7	taken	take	VERB
eurjchem-503	14	8	by	by	ADP
eurjchem-503	14	9	other	other	ADJ
eurjchem-503	14	10	research	research	NOUN
eurjchem-503	14	11	groups	group	NOUN
eurjchem-503	14	12	towards	towards	ADP
eurjchem-503	14	13	the	the	DET
eurjchem-503	14	14	synthesis	synthesis	NOUN
eurjchem-503	14	15	of	of	ADP
eurjchem-503	14	16	reserpine	reserpine	NOUN
eurjchem-503	14	17	and	and	CCONJ
eurjchem-503	14	18	various	various	ADJ
eurjchem-503	14	19	synthetic	synthetic	ADJ
eurjchem-503	14	20	strategies	strategy	NOUN
eurjchem-503	14	21	have	have	AUX
eurjchem-503	14	22	been	be	AUX
eurjchem-503	14	23	developed	develop	VERB
eurjchem-503	14	24	and	and	CCONJ
eurjchem-503	14	25	applied	apply	VERB
eurjchem-503	14	26	to	to	ADP
eurjchem-503	14	27	the	the	DET
eurjchem-503	14	28	synthesis	synthesis	NOUN
eurjchem-503	14	29	of	of	ADP
eurjchem-503	14	30	reserpine	reserpine	NOUN
eurjchem-503	14	31	.	.	PUNCT
eurjchem-503	15	1	for	for	ADP
eurjchem-503	15	2	example	example	NOUN
eurjchem-503	15	3	,	,	PUNCT
eurjchem-503	15	4	pearlman	pearlman	PROPN
eurjchem-503	15	5	developed	develop	VERB
eurjchem-503	15	6	an	an	DET
eurjchem-503	15	7	intramolecular	intramolecular	ADJ
eurjchem-503	15	8	photoinduced	photoinduce	VERB
eurjchem-503	15	9	[	[	X
eurjchem-503	15	10	2	2	NUM
eurjchem-503	15	11	+	+	NOUN
eurjchem-503	15	12	2	2	NUM
eurjchem-503	15	13	]	]	PUNCT
eurjchem-503	15	14	cyclization	cyclization	NOUN
eurjchem-503	15	15	strategy	strategy	NOUN
eurjchem-503	15	16	using	use	VERB
eurjchem-503	15	17	1,4‐dihydrobenzoic	1,4‐dihydrobenzoic	NUM
eurjchem-503	15	18	acid	acid	NOUN
eurjchem-503	15	19	to	to	PART
eurjchem-503	15	20	generate	generate	VERB
eurjchem-503	15	21	the	the	DET
eurjchem-503	15	22	required	require	VERB
eurjchem-503	15	23	woodward	woodward	NOUN
eurjchem-503	15	24	ring	ring	PROPN
eurjchem-503	15	25	e	e	PROPN
eurjchem-503	15	26	precursor	precursor	NOUN
eurjchem-503	15	27	[	[	X
eurjchem-503	15	28	12	12	NUM
eurjchem-503	15	29	]	]	PUNCT
eurjchem-503	15	30	.	.	PUNCT
eurjchem-503	16	1	later	later	ADV
eurjchem-503	16	2	wender	wender	NOUN
eurjchem-503	16	3	and	and	CCONJ
eurjchem-503	16	4	co‐workers	co‐worker	NOUN
eurjchem-503	16	5	established	establish	VERB
eurjchem-503	16	6	a	a	DET
eurjchem-503	16	7	new	new	ADJ
eurjchem-503	16	8	method	method	NOUN
eurjchem-503	16	9	to	to	PART
eurjchem-503	16	10	make	make	VERB
eurjchem-503	16	11	d	d	NOUN
eurjchem-503	16	12	/	/	SYM
eurjchem-503	16	13	e	e	NOUN
eurjchem-503	16	14	ring	ring	NOUN
eurjchem-503	16	15	unit	unit	NOUN
eurjchem-503	16	16	using	use	VERB
eurjchem-503	16	17	methyl	methyl	NOUN
eurjchem-503	16	18	1,2‐dihydropyridine‐1‐	1,2‐dihydropyridine‐1‐	NUM
eurjchem-503	16	19	carboxylate	carboxylate	NOUN
eurjchem-503	16	20	,	,	PUNCT
eurjchem-503	16	21	and	and	CCONJ
eurjchem-503	16	22	which	which	PRON
eurjchem-503	16	23	underwent	undergo	VERB
eurjchem-503	16	24	a	a	DET
eurjchem-503	16	25	diels‐alder	diels‐alder	NOUN
eurjchem-503	16	26	reaction	reaction	NOUN
eurjchem-503	16	27	and	and	CCONJ
eurjchem-503	16	28	then	then	ADV
eurjchem-503	16	29	cope	cope	VERB
eurjchem-503	16	30	rearrangement	rearrangement	NOUN
eurjchem-503	16	31	to	to	PART
eurjchem-503	16	32	produce	produce	VERB
eurjchem-503	16	33	a	a	DET
eurjchem-503	16	34	cis‐hydroisoquinoline	cis‐hydroisoquinoline	NOUN
eurjchem-503	16	35	intermediate	intermediate	NOUN
eurjchem-503	16	36	[	[	X
eurjchem-503	16	37	13,14,21	13,14,21	NUM
eurjchem-503	16	38	]	]	PUNCT
eurjchem-503	16	39	.	.	PUNCT
eurjchem-503	17	1	martin	martin	PROPN
eurjchem-503	17	2	and	and	CCONJ
eurjchem-503	17	3	associates	associate	NOUN
eurjchem-503	17	4	developed	develop	VERB
eurjchem-503	17	5	a	a	DET
eurjchem-503	17	6	general	general	ADJ
eurjchem-503	17	7	protocol	protocol	NOUN
eurjchem-503	17	8	following	follow	VERB
eurjchem-503	17	9	an	an	DET
eurjchem-503	17	10	intramolecular	intramolecular	ADJ
eurjchem-503	17	11	diels‐alder	diels‐alder	NOUN
eurjchem-503	17	12	reaction	reaction	NOUN
eurjchem-503	17	13	to	to	PART
eurjchem-503	17	14	generate	generate	VERB
eurjchem-503	17	15	a	a	DET
eurjchem-503	17	16	hydroisoquinoline	hydroisoquinoline	NOUN
eurjchem-503	17	17	ring	ring	NOUN
eurjchem-503	17	18	system	system	NOUN
eurjchem-503	17	19	which	which	PRON
eurjchem-503	17	20	contains	contain	VERB
eurjchem-503	17	21	the	the	DET
eurjchem-503	17	22	trisubstituted	trisubstituted	ADJ
eurjchem-503	17	23	d	d	PROPN
eurjchem-503	17	24	/	/	SYM
eurjchem-503	17	25	e	e	NOUN
eurjchem-503	17	26	ring	ring	NOUN
eurjchem-503	17	27	unit	unit	NOUN
eurjchem-503	17	28	[	[	X
eurjchem-503	17	29	15,16	15,16	NUM
eurjchem-503	17	30	]	]	PUNCT
eurjchem-503	17	31	.	.	PUNCT
eurjchem-503	18	1	stork	stork	NOUN
eurjchem-503	18	2	and	and	CCONJ
eurjchem-503	18	3	co‐workers	co‐worker	NOUN
eurjchem-503	18	4	used	use	VERB
eurjchem-503	18	5	enantiomerically	enantiomerically	ADV
eurjchem-503	18	6	pure	pure	ADJ
eurjchem-503	18	7	3‐	3‐	NUM
eurjchem-503	18	8	cyclohexenecarboxylic	cyclohexenecarboxylic	NOUN
eurjchem-503	18	9	acid	acid	NOUN
eurjchem-503	18	10	to	to	PART
eurjchem-503	18	11	produce	produce	VERB
eurjchem-503	18	12	a	a	DET
eurjchem-503	18	13	penta	penta	NOUN
eurjchem-503	18	14	substituted	substitute	VERB
eurjchem-503	18	15	carbocycle	carbocycle	NOUN
eurjchem-503	18	16	representing	represent	VERB
eurjchem-503	18	17	ring	ring	NOUN
eurjchem-503	18	18	e	e	NOUN
eurjchem-503	18	19	via	via	ADP
eurjchem-503	18	20	a	a	DET
eurjchem-503	18	21	stereocontrolled	stereocontrolle	VERB
eurjchem-503	18	22	building	building	NOUN
eurjchem-503	18	23	of	of	ADP
eurjchem-503	18	24	the	the	DET
eurjchem-503	18	25	required	require	VERB
eurjchem-503	18	26	functionalities	functionality	NOUN
eurjchem-503	18	27	[	[	X
eurjchem-503	18	28	17	17	NUM
eurjchem-503	18	29	]	]	PUNCT
eurjchem-503	18	30	.	.	PUNCT
eurjchem-503	19	1	we	we	PRON
eurjchem-503	19	2	have	have	AUX
eurjchem-503	19	3	considered	consider	VERB
eurjchem-503	19	4	the	the	DET
eurjchem-503	19	5	enamide	enamide	ADJ
eurjchem-503	19	6	photocyclization	photocyclization	NOUN
eurjchem-503	19	7	approach	approach	NOUN
eurjchem-503	19	8	to	to	ADP
eurjchem-503	19	9	the	the	DET
eurjchem-503	19	10	total	total	ADJ
eurjchem-503	19	11	synthesis	synthesis	NOUN
eurjchem-503	19	12	of	of	ADP
eurjchem-503	19	13	(	(	PUNCT
eurjchem-503	19	14	±)‐reserpine	±)‐reserpine	X
eurjchem-503	19	15	,	,	PUNCT
eurjchem-503	19	16	1	1	X
eurjchem-503	19	17	.	.	X
eurjchem-503	20	1	this	this	DET
eurjchem-503	20	2	approach	approach	NOUN
eurjchem-503	20	3	is	be	AUX
eurjchem-503	20	4	continuation	continuation	NOUN
eurjchem-503	20	5	of	of	ADP
eurjchem-503	20	6	our	our	PRON
eurjchem-503	20	7	previously	previously	ADV
eurjchem-503	20	8	established	establish	VERB
eurjchem-503	20	9	reductive	reductive	ADJ
eurjchem-503	20	10	photocyclization	photocyclization	NOUN
eurjchem-503	20	11	of	of	ADP
eurjchem-503	20	12	enamides	enamides	PROPN
eurjchem-503	20	13	methodology	methodology	PROPN
eurjchem-503	20	14	;	;	PUNCT
eurjchem-503	20	15	we	we	PRON
eurjchem-503	20	16	have	have	AUX
eurjchem-503	20	17	reported	report	VERB
eurjchem-503	20	18	efficient	efficient	ADJ
eurjchem-503	20	19	synthesis	synthesis	NOUN
eurjchem-503	20	20	of	of	ADP
eurjchem-503	20	21	various	various	ADJ
eurjchem-503	20	22	natural	natural	ADJ
eurjchem-503	20	23	alkaloids	alkaloid	NOUN
eurjchem-503	20	24	using	use	VERB
eurjchem-503	20	25	this	this	DET
eurjchem-503	20	26	method	method	NOUN
eurjchem-503	21	1	[	[	X
eurjchem-503	21	2	22,23	22,23	NOUN
eurjchem-503	21	3	]	]	X
eurjchem-503	21	4	.	.	PUNCT
eurjchem-503	22	1	we	we	PRON
eurjchem-503	22	2	wanted	want	VERB
eurjchem-503	22	3	to	to	PART
eurjchem-503	22	4	further	far	ADV
eurjchem-503	22	5	explore	explore	VERB
eurjchem-503	22	6	this	this	DET
eurjchem-503	22	7	protocol	protocol	NOUN
eurjchem-503	22	8	towards	towards	ADP
eurjchem-503	22	9	the	the	DET
eurjchem-503	22	10	synthesis	synthesis	NOUN
eurjchem-503	22	11	of	of	ADP
eurjchem-503	22	12	structurally	structurally	ADV
eurjchem-503	22	13	more	more	ADV
eurjchem-503	22	14	complicated	complicated	ADJ
eurjchem-503	22	15	and	and	CCONJ
eurjchem-503	22	16	medicinal	medicinal	ADJ
eurjchem-503	22	17	important	important	ADJ
eurjchem-503	22	18	natural	natural	ADJ
eurjchem-503	22	19	alkaloid	alkaloid	NOUN
eurjchem-503	22	20	,	,	PUNCT
eurjchem-503	22	21	(	(	PUNCT
eurjchem-503	22	22	±)‐	±)‐	ADJ
eurjchem-503	22	23	reserpine	reserpine	NOUN
eurjchem-503	22	24	.	.	PUNCT
eurjchem-503	23	1	as	as	SCONJ
eurjchem-503	23	2	described	describe	VERB
eurjchem-503	23	3	above	above	ADV
eurjchem-503	23	4	,	,	PUNCT
eurjchem-503	23	5	our	our	PRON
eurjchem-503	23	6	aim	aim	NOUN
eurjchem-503	23	7	is	be	AUX
eurjchem-503	23	8	the	the	DET
eurjchem-503	23	9	enamidephotocyclization	enamidephotocyclization	NOUN
eurjchem-503	23	10	based	base	VERB
eurjchem-503	23	11	construction	construction	NOUN
eurjchem-503	23	12	of	of	ADP
eurjchem-503	23	13	the	the	DET
eurjchem-503	23	14	key	key	ADJ
eurjchem-503	23	15	pentacyclic	pentacyclic	ADJ
eurjchem-503	23	16	motif	motif	NOUN
eurjchem-503	23	17	14	14	NUM
eurjchem-503	23	18	.	.	PUNCT
eurjchem-503	24	1	herein	herein	NOUN
eurjchem-503	24	2	we	we	PRON
eurjchem-503	24	3	illustrate	illustrate	VERB
eurjchem-503	24	4	the	the	DET
eurjchem-503	24	5	synthesis	synthesis	NOUN
eurjchem-503	24	6	of	of	ADP
eurjchem-503	24	7	pentacyclic	pentacyclic	ADJ
eurjchem-503	24	8	key	key	ADJ
eurjchem-503	24	9	intermediate	intermediate	ADJ
eurjchem-503	24	10	14	14	NUM
eurjchem-503	24	11	from	from	ADP
eurjchem-503	24	12	naturally	naturally	ADV
eurjchem-503	24	13	occurring	occur	VERB
eurjchem-503	24	14	harmaline	harmaline	NOUN
eurjchem-503	24	15	,	,	PUNCT
eurjchem-503	24	16	2	2	NUM
eurjchem-503	24	17	[	[	X
eurjchem-503	24	18	24	24	NUM
eurjchem-503	24	19	]	]	PUNCT
eurjchem-503	24	20	.	.	PUNCT
eurjchem-503	25	1	yar	yar	PROPN
eurjchem-503	25	2	et	et	PROPN
eurjchem-503	25	3	al	al	PROPN
eurjchem-503	25	4	.	.	PUNCT
eurjchem-503	25	5	/	/	SYM
eurjchem-503	25	6	european	european	PROPN
eurjchem-503	25	7	journal	journal	PROPN
eurjchem-503	25	8	of	of	ADP
eurjchem-503	25	9	chemistry	chemistry	NOUN
eurjchem-503	25	10	3	3	NUM
eurjchem-503	25	11	(	(	PUNCT
eurjchem-503	25	12	1	1	NUM
eurjchem-503	25	13	)	)	PUNCT
eurjchem-503	25	14	(	(	PUNCT
eurjchem-503	25	15	2012	2012	NUM
eurjchem-503	25	16	)	)	PUNCT
eurjchem-503	25	17	26‐31	26‐31	ADV
eurjchem-503	25	18	27	27	NUM
eurjchem-503	25	19	n	n	NOUN
eurjchem-503	25	20	h	h	NOUN
eurjchem-503	25	21	n	n	CCONJ
eurjchem-503	25	22	meo	meo	PROPN
eurjchem-503	25	23	h	h	NOUN
eurjchem-503	25	24	meooc	meooc	NOUN
eurjchem-503	26	1	o	o	INTJ
eurjchem-503	26	2	h	h	NOUN
eurjchem-503	26	3	h	h	NOUN
eurjchem-503	27	1	ome	ome	INTJ
eurjchem-503	27	2	o	o	INTJ
eurjchem-503	27	3	ome	ome	INTJ
eurjchem-503	27	4	ome	ome	INTJ
eurjchem-503	27	5	ome	ome	ADP
eurjchem-503	27	6	a	a	DET
eurjchem-503	27	7	b	b	NOUN
eurjchem-503	27	8	c	c	NOUN
eurjchem-503	27	9	d	d	PROPN
eurjchem-503	27	10	e	e	PROPN
eurjchem-503	27	11	3	3	NUM
eurjchem-503	27	12	11	11	NUM
eurjchem-503	27	13	15	15	NUM
eurjchem-503	27	14	16	16	NUM
eurjchem-503	27	15	17	17	NUM
eurjchem-503	27	16	18	18	NUM
eurjchem-503	27	17	19	19	NUM
eurjchem-503	27	18	20	20	NUM
eurjchem-503	27	19	21	21	NUM
eurjchem-503	27	20	1	1	NUM
eurjchem-503	27	21	1	1	NUM
eurjchem-503	27	22	2	2	NUM
eurjchem-503	27	23	4	4	NUM
eurjchem-503	27	24	56	56	NUM
eurjchem-503	27	25	78	78	NUM
eurjchem-503	27	26	9	9	NUM
eurjchem-503	27	27	10	10	NUM
eurjchem-503	27	28	12	12	NUM
eurjchem-503	27	29	13	13	NUM
eurjchem-503	27	30	14	14	NUM
eurjchem-503	27	31	figure	figure	NOUN
eurjchem-503	27	32	1	1	NUM
eurjchem-503	27	33	.	.	PUNCT
eurjchem-503	27	34	reserpine	reserpine	NOUN
eurjchem-503	27	35	,	,	PUNCT
eurjchem-503	27	36	1	1	NUM
eurjchem-503	27	37	.	.	SYM
eurjchem-503	27	38	2	2	NUM
eurjchem-503	27	39	.	.	X
eurjchem-503	27	40	experimental	experimental	ADJ
eurjchem-503	27	41	2.1	2.1	NUM
eurjchem-503	27	42	.	.	PUNCT
eurjchem-503	28	1	instrumentation	instrumentation	NOUN
eurjchem-503	28	2	chromatography	chromatography	NOUN
eurjchem-503	28	3	:	:	PUNCT
eurjchem-503	28	4	flash	flash	PROPN
eurjchem-503	28	5	chromatography	chromatography	NOUN
eurjchem-503	28	6	was	be	AUX
eurjchem-503	28	7	performed	perform	VERB
eurjchem-503	28	8	on	on	ADP
eurjchem-503	28	9	silica	silica	NOUN
eurjchem-503	28	10	gel	gel	NOUN
eurjchem-503	28	11	(	(	PUNCT
eurjchem-503	28	12	merck	merck	PROPN
eurjchem-503	28	13	kieselgel	kieselgel	PROPN
eurjchem-503	28	14	60	60	NUM
eurjchem-503	28	15	,	,	PUNCT
eurjchem-503	28	16	230‐400	230‐400	NUM
eurjchem-503	28	17	mesh	mesh	NOUN
eurjchem-503	28	18	)	)	PUNCT
eurjchem-503	28	19	unless	unless	SCONJ
eurjchem-503	28	20	otherwise	otherwise	ADV
eurjchem-503	28	21	stated	state	VERB
eurjchem-503	28	22	.	.	PUNCT
eurjchem-503	29	1	tlc	tlc	PROPN
eurjchem-503	29	2	was	be	AUX
eurjchem-503	29	3	performed	perform	VERB
eurjchem-503	29	4	on	on	ADP
eurjchem-503	29	5	aluminium‐backed	aluminium‐backe	VERB
eurjchem-503	29	6	silica	silica	NOUN
eurjchem-503	29	7	plates	plate	NOUN
eurjchem-503	29	8	(	(	PUNCT
eurjchem-503	29	9	60f254	60f254	NOUN
eurjchem-503	29	10	,	,	PUNCT
eurjchem-503	29	11	0.2	0.2	NUM
eurjchem-503	29	12	mm	mm	NOUN
eurjchem-503	29	13	)	)	PUNCT
eurjchem-503	29	14	.	.	PUNCT
eurjchem-503	30	1	the	the	DET
eurjchem-503	30	2	photochemical	photochemical	ADJ
eurjchem-503	30	3	reactions	reaction	NOUN
eurjchem-503	30	4	were	be	AUX
eurjchem-503	30	5	carried	carry	VERB
eurjchem-503	30	6	out	out	ADP
eurjchem-503	30	7	using	use	VERB
eurjchem-503	30	8	a	a	DET
eurjchem-503	30	9	high	high	ADJ
eurjchem-503	30	10	pressure	pressure	NOUN
eurjchem-503	30	11	(	(	PUNCT
eurjchem-503	30	12	100	100	NUM
eurjchem-503	30	13	w	w	NOUN
eurjchem-503	30	14	)	)	PUNCT
eurjchem-503	30	15	mercury	mercury	NOUN
eurjchem-503	30	16	lamp	lamp	NOUN
eurjchem-503	30	17	model	model	NOUN
eurjchem-503	30	18	number	number	NOUN
eurjchem-503	30	19	el‐60	el‐60	PROPN
eurjchem-503	30	20	.	.	PUNCT
eurjchem-503	31	1	all	all	DET
eurjchem-503	31	2	the	the	DET
eurjchem-503	31	3	commercially	commercially	ADV
eurjchem-503	31	4	available	available	ADJ
eurjchem-503	31	5	reagents	reagent	NOUN
eurjchem-503	31	6	were	be	AUX
eurjchem-503	31	7	used	use	VERB
eurjchem-503	31	8	as	as	SCONJ
eurjchem-503	31	9	obtained	obtain	VERB
eurjchem-503	31	10	from	from	ADP
eurjchem-503	31	11	wako	wako	PROPN
eurjchem-503	31	12	chemical	chemical	PROPN
eurjchem-503	31	13	co.	co.	PROPN
eurjchem-503	31	14	japan	japan	PROPN
eurjchem-503	31	15	.	.	PUNCT
eurjchem-503	32	1	all	all	DET
eurjchem-503	32	2	the	the	DET
eurjchem-503	32	3	solvents	solvent	NOUN
eurjchem-503	32	4	were	be	AUX
eurjchem-503	32	5	used	use	VERB
eurjchem-503	32	6	as	as	SCONJ
eurjchem-503	32	7	obtained	obtain	VERB
eurjchem-503	32	8	,	,	PUNCT
eurjchem-503	32	9	except	except	SCONJ
eurjchem-503	32	10	thf	thf	NOUN
eurjchem-503	32	11	and	and	CCONJ
eurjchem-503	32	12	et2o	et2o	PROPN
eurjchem-503	32	13	were	be	AUX
eurjchem-503	32	14	dried	dry	VERB
eurjchem-503	32	15	over	over	ADP
eurjchem-503	32	16	na	na	NOUN
eurjchem-503	32	17	in	in	ADP
eurjchem-503	32	18	benzophenone	benzophenone	NOUN
eurjchem-503	32	19	.	.	PUNCT
eurjchem-503	33	1	ir	ir	PROPN
eurjchem-503	33	2	spectra	spectra	PROPN
eurjchem-503	33	3	were	be	AUX
eurjchem-503	33	4	recorded	record	VERB
eurjchem-503	33	5	on	on	ADP
eurjchem-503	33	6	a	a	DET
eurjchem-503	33	7	jasco	jasco	PROPN
eurjchem-503	33	8	a‐302	a‐302	NOUN
eurjchem-503	33	9	ir	ir	PROPN
eurjchem-503	33	10	spectrophotometer	spectrophotometer	NOUN
eurjchem-503	33	11	.	.	PUNCT
eurjchem-503	34	1	1h‐nmr	1h‐nmr	NUM
eurjchem-503	34	2	spectra	spectra	NOUN
eurjchem-503	34	3	were	be	AUX
eurjchem-503	34	4	recorded	record	VERB
eurjchem-503	34	5	on	on	ADP
eurjchem-503	34	6	bruker	bruker	ADJ
eurjchem-503	34	7	nmr	nmr	NOUN
eurjchem-503	34	8	400	400	NUM
eurjchem-503	34	9	or	or	CCONJ
eurjchem-503	34	10	500	500	NUM
eurjchem-503	34	11	mhz	mhz	NOUN
eurjchem-503	34	12	spectrometer	spectrometer	NOUN
eurjchem-503	34	13	and	and	CCONJ
eurjchem-503	34	14	chemical	chemical	NOUN
eurjchem-503	34	15	shifts	shift	NOUN
eurjchem-503	34	16	were	be	AUX
eurjchem-503	34	17	calculated	calculate	VERB
eurjchem-503	34	18	with	with	ADP
eurjchem-503	34	19	reference	reference	NOUN
eurjchem-503	34	20	to	to	ADP
eurjchem-503	34	21	cdcl3	cdcl3	NOUN
eurjchem-503	34	22	(	(	PUNCT
eurjchem-503	34	23	δ	δ	PROPN
eurjchem-503	34	24	7.25	7.25	NUM
eurjchem-503	34	25	ppm	ppm	NOUN
eurjchem-503	34	26	)	)	PUNCT
eurjchem-503	34	27	.	.	PUNCT
eurjchem-503	35	1	mass	mass	PROPN
eurjchem-503	35	2	spectra	spectra	PROPN
eurjchem-503	35	3	were	be	AUX
eurjchem-503	35	4	recorded	record	VERB
eurjchem-503	35	5	on	on	ADP
eurjchem-503	35	6	a	a	DET
eurjchem-503	35	7	varian	varian	NOUN
eurjchem-503	35	8	mat	mat	NOUN
eurjchem-503	35	9	312	312	NUM
eurjchem-503	35	10	double	double	ADJ
eurjchem-503	35	11	focusing	focus	VERB
eurjchem-503	35	12	spectrometer	spectrometer	NOUN
eurjchem-503	35	13	,	,	PUNCT
eurjchem-503	35	14	connected	connect	VERB
eurjchem-503	35	15	to	to	ADP
eurjchem-503	35	16	an	an	DET
eurjchem-503	35	17	ibm‐at	ibm‐at	ADJ
eurjchem-503	35	18	compatible	compatible	ADJ
eurjchem-503	35	19	pc	pc	NOUN
eurjchem-503	35	20	computer	computer	NOUN
eurjchem-503	35	21	system	system	NOUN
eurjchem-503	35	22	.	.	PUNCT
eurjchem-503	36	1	2.2	2.2	NUM
eurjchem-503	36	2	.	.	PUNCT
eurjchem-503	36	3	synthesis	synthesis	NOUN
eurjchem-503	36	4	2.2.1	2.2.1	NUM
eurjchem-503	36	5	.	.	PUNCT
eurjchem-503	37	1	11‐methoxy‐2,3,4,9‐tetrahydro‐2‐(benzoyl)‐1‐	11‐methoxy‐2,3,4,9‐tetrahydro‐2‐(benzoyl)‐1‐	ADJ
eurjchem-503	37	2	methylen‐1h‐pyrido[3,4]‐indole	methylen‐1h‐pyrido[3,4]‐indole	NOUN
eurjchem-503	37	3	(	(	PUNCT
eurjchem-503	37	4	4	4	NUM
eurjchem-503	37	5	)	)	PUNCT
eurjchem-503	37	6	benzoyl	benzoyl	ADJ
eurjchem-503	37	7	chloride	chloride	NOUN
eurjchem-503	37	8	(	(	PUNCT
eurjchem-503	37	9	310	310	NUM
eurjchem-503	37	10	mg	mg	PROPN
eurjchem-503	37	11	,	,	PUNCT
eurjchem-503	37	12	2.20	2.20	NUM
eurjchem-503	37	13	mmol	mmol	NOUN
eurjchem-503	37	14	)	)	PUNCT
eurjchem-503	37	15	was	be	AUX
eurjchem-503	37	16	added	add	VERB
eurjchem-503	37	17	dropwise	dropwise	NOUN
eurjchem-503	37	18	to	to	ADP
eurjchem-503	37	19	ice‐cooled	ice‐coole	VERB
eurjchem-503	37	20	,	,	PUNCT
eurjchem-503	37	21	stirred	stir	VERB
eurjchem-503	37	22	solution	solution	NOUN
eurjchem-503	37	23	of	of	ADP
eurjchem-503	37	24	harmaline	harmaline	PROPN
eurjchem-503	37	25	2	2	NUM
eurjchem-503	37	26	(	(	PUNCT
eurjchem-503	37	27	220	220	NUM
eurjchem-503	37	28	mg	mg	NOUN
eurjchem-503	37	29	,	,	PUNCT
eurjchem-503	37	30	1.03	1.03	NUM
eurjchem-503	37	31	mmol	mmol	NOUN
eurjchem-503	37	32	)	)	PUNCT
eurjchem-503	37	33	and	and	CCONJ
eurjchem-503	37	34	triethylamine	triethylamine	NOUN
eurjchem-503	37	35	(	(	PUNCT
eurjchem-503	37	36	600	600	NUM
eurjchem-503	37	37	mg	mg	PROPN
eurjchem-503	37	38	,	,	PUNCT
eurjchem-503	37	39	5.93	5.93	NUM
eurjchem-503	37	40	mmol	mmol	NOUN
eurjchem-503	37	41	)	)	PUNCT
eurjchem-503	37	42	in	in	ADP
eurjchem-503	37	43	anhydrous	anhydrous	ADJ
eurjchem-503	37	44	benzene	benzene	NOUN
eurjchem-503	37	45	(	(	PUNCT
eurjchem-503	37	46	70	70	NUM
eurjchem-503	37	47	ml	ml	NOUN
eurjchem-503	37	48	)	)	PUNCT
eurjchem-503	37	49	.	.	PUNCT
eurjchem-503	38	1	after	after	ADP
eurjchem-503	38	2	being	be	AUX
eurjchem-503	38	3	stirred	stir	VERB
eurjchem-503	38	4	at	at	ADP
eurjchem-503	38	5	room	room	NOUN
eurjchem-503	38	6	temperature	temperature	NOUN
eurjchem-503	38	7	for	for	ADP
eurjchem-503	38	8	30	30	NUM
eurjchem-503	38	9	minutes	minute	NOUN
eurjchem-503	38	10	,	,	PUNCT
eurjchem-503	38	11	the	the	DET
eurjchem-503	38	12	reaction	reaction	NOUN
eurjchem-503	38	13	mixture	mixture	NOUN
eurjchem-503	38	14	was	be	AUX
eurjchem-503	38	15	filtered	filter	VERB
eurjchem-503	38	16	to	to	PART
eurjchem-503	38	17	remove	remove	VERB
eurjchem-503	38	18	triethylamine	triethylamine	NOUN
eurjchem-503	38	19	hydrochloride	hydrochloride	NOUN
eurjchem-503	38	20	.	.	PUNCT
eurjchem-503	39	1	the	the	DET
eurjchem-503	39	2	filtrate	filtrate	NOUN
eurjchem-503	39	3	was	be	AUX
eurjchem-503	39	4	evaporated	evaporate	VERB
eurjchem-503	39	5	to	to	PART
eurjchem-503	39	6	give	give	VERB
eurjchem-503	39	7	the	the	DET
eurjchem-503	39	8	unstable	unstable	ADJ
eurjchem-503	39	9	enamide	enamide	NOUN
eurjchem-503	39	10	4	4	NUM
eurjchem-503	39	11	(	(	PUNCT
eurjchem-503	39	12	315	315	NUM
eurjchem-503	39	13	mg	mg	NOUN
eurjchem-503	39	14	,	,	PUNCT
eurjchem-503	39	15	96	96	NUM
eurjchem-503	39	16	%	%	NOUN
eurjchem-503	39	17	)	)	PUNCT
eurjchem-503	39	18	as	as	ADP
eurjchem-503	39	19	a	a	DET
eurjchem-503	39	20	brown	brown	ADJ
eurjchem-503	39	21	gum	gum	NOUN
eurjchem-503	39	22	,	,	PUNCT
eurjchem-503	39	23	which	which	PRON
eurjchem-503	39	24	was	be	AUX
eurjchem-503	39	25	used	use	VERB
eurjchem-503	39	26	for	for	ADP
eurjchem-503	39	27	irradiation	irradiation	NOUN
eurjchem-503	39	28	without	without	ADP
eurjchem-503	39	29	purification	purification	NOUN
eurjchem-503	39	30	(	(	PUNCT
eurjchem-503	39	31	scheme	scheme	NOUN
eurjchem-503	39	32	1	1	NUM
eurjchem-503	39	33	)	)	PUNCT
eurjchem-503	39	34	.	.	PUNCT
eurjchem-503	40	1	2.2.2	2.2.2	X
eurjchem-503	40	2	.	.	PUNCT
eurjchem-503	41	1	benzo[g]indolo[2,3‐a]quinolizin‐5‐(7h)‐one‐8,13‐	benzo[g]indolo[2,3‐a]quinolizin‐5‐(7h)‐one‐8,13‐	PROPN
eurjchem-503	41	2	dihydro‐11‐methoxy	dihydro‐11‐methoxy	PROPN
eurjchem-503	41	3	(	(	PUNCT
eurjchem-503	41	4	5	5	NUM
eurjchem-503	41	5	)	)	PUNCT
eurjchem-503	41	6	sodium	sodium	NOUN
eurjchem-503	41	7	borohydride	borohydride	NOUN
eurjchem-503	41	8	(	(	PUNCT
eurjchem-503	41	9	350	350	NUM
eurjchem-503	41	10	mg	mg	PROPN
eurjchem-503	41	11	,	,	PUNCT
eurjchem-503	41	12	9.26	9.26	NUM
eurjchem-503	41	13	mmol	mmol	NOUN
eurjchem-503	41	14	)	)	PUNCT
eurjchem-503	41	15	and	and	CCONJ
eurjchem-503	41	16	methanol	methanol	NOUN
eurjchem-503	41	17	(	(	PUNCT
eurjchem-503	41	18	45	45	NUM
eurjchem-503	41	19	ml	ml	NOUN
eurjchem-503	41	20	)	)	PUNCT
eurjchem-503	41	21	were	be	AUX
eurjchem-503	41	22	added	add	VERB
eurjchem-503	41	23	successively	successively	ADV
eurjchem-503	41	24	to	to	ADP
eurjchem-503	41	25	a	a	DET
eurjchem-503	41	26	stirred	stir	VERB
eurjchem-503	41	27	solution	solution	NOUN
eurjchem-503	41	28	of	of	ADP
eurjchem-503	41	29	the	the	DET
eurjchem-503	41	30	enamide	enamide	ADJ
eurjchem-503	41	31	4	4	NUM
eurjchem-503	41	32	(	(	PUNCT
eurjchem-503	41	33	315	315	NUM
eurjchem-503	41	34	mg	mg	PROPN
eurjchem-503	41	35	,	,	PUNCT
eurjchem-503	41	36	0.989	0.989	NUM
eurjchem-503	41	37	mmol	mmol	NOUN
eurjchem-503	41	38	)	)	PUNCT
eurjchem-503	41	39	in	in	ADP
eurjchem-503	41	40	acetonitrile	acetonitrile	NOUN
eurjchem-503	41	41	(	(	PUNCT
eurjchem-503	41	42	150	150	NUM
eurjchem-503	41	43	ml	ml	NOUN
eurjchem-503	41	44	)	)	PUNCT
eurjchem-503	41	45	at	at	ADP
eurjchem-503	41	46	room	room	NOUN
eurjchem-503	41	47	temperature	temperature	NOUN
eurjchem-503	41	48	.	.	PUNCT
eurjchem-503	42	1	when	when	SCONJ
eurjchem-503	42	2	the	the	DET
eurjchem-503	42	3	added	add	VERB
eurjchem-503	42	4	sodium	sodium	NOUN
eurjchem-503	42	5	borohydride	borohydride	NOUN
eurjchem-503	42	6	had	have	AUX
eurjchem-503	42	7	dissolved	dissolve	VERB
eurjchem-503	42	8	,	,	PUNCT
eurjchem-503	42	9	the	the	DET
eurjchem-503	42	10	resulting	result	VERB
eurjchem-503	42	11	solution	solution	NOUN
eurjchem-503	42	12	was	be	AUX
eurjchem-503	42	13	cooled	cool	VERB
eurjchem-503	42	14	to	to	ADP
eurjchem-503	42	15	0‐5	0‐5	PRON
eurjchem-503	42	16	oc	oc	VERB
eurjchem-503	42	17	and	and	CCONJ
eurjchem-503	42	18	irradiated	irradiate	VERB
eurjchem-503	42	19	for	for	ADP
eurjchem-503	42	20	6	6	NUM
eurjchem-503	42	21	hours	hour	NOUN
eurjchem-503	42	22	.	.	PUNCT
eurjchem-503	43	1	the	the	DET
eurjchem-503	43	2	reaction	reaction	NOUN
eurjchem-503	43	3	mixture	mixture	NOUN
eurjchem-503	43	4	was	be	AUX
eurjchem-503	43	5	filtered	filter	VERB
eurjchem-503	43	6	and	and	CCONJ
eurjchem-503	43	7	evaporated	evaporate	VERB
eurjchem-503	43	8	under	under	ADP
eurjchem-503	43	9	reduced	reduced	ADJ
eurjchem-503	43	10	pressure	pressure	NOUN
eurjchem-503	43	11	.	.	PUNCT
eurjchem-503	44	1	10	10	NUM
eurjchem-503	44	2	%	%	NOUN
eurjchem-503	44	3	sodium	sodium	NOUN
eurjchem-503	44	4	bicarbonate	bicarbonate	NOUN
eurjchem-503	44	5	was	be	AUX
eurjchem-503	44	6	added	add	VERB
eurjchem-503	44	7	and	and	CCONJ
eurjchem-503	44	8	extracted	extract	VERB
eurjchem-503	44	9	with	with	ADP
eurjchem-503	44	10	ethyl	ethyl	PROPN
eurjchem-503	44	11	acetate	acetate	NOUN
eurjchem-503	44	12	.	.	PUNCT
eurjchem-503	45	1	the	the	DET
eurjchem-503	45	2	organic	organic	ADJ
eurjchem-503	45	3	layer	layer	NOUN
eurjchem-503	45	4	was	be	AUX
eurjchem-503	45	5	dried	dry	VERB
eurjchem-503	45	6	over	over	ADP
eurjchem-503	45	7	anhydrous	anhydrous	ADJ
eurjchem-503	45	8	sodium	sodium	NOUN
eurjchem-503	45	9	sulfate	sulfate	NOUN
eurjchem-503	45	10	and	and	CCONJ
eurjchem-503	45	11	evaporated	evaporate	VERB
eurjchem-503	45	12	to	to	PART
eurjchem-503	45	13	give	give	VERB
eurjchem-503	45	14	a	a	DET
eurjchem-503	45	15	solid	solid	NOUN
eurjchem-503	45	16	,	,	PUNCT
eurjchem-503	45	17	which	which	PRON
eurjchem-503	45	18	was	be	AUX
eurjchem-503	45	19	recrystallized	recrystallize	VERB
eurjchem-503	45	20	from	from	ADP
eurjchem-503	45	21	methanol	methanol	NOUN
eurjchem-503	45	22	to	to	PART
eurjchem-503	45	23	give	give	VERB
eurjchem-503	45	24	a	a	DET
eurjchem-503	45	25	lactam	lactam	NOUN
eurjchem-503	45	26	5	5	NUM
eurjchem-503	45	27	as	as	ADP
eurjchem-503	45	28	light	light	ADJ
eurjchem-503	45	29	yellow	yellow	ADJ
eurjchem-503	45	30	crystals	crystal	NOUN
eurjchem-503	45	31	(	(	PUNCT
eurjchem-503	45	32	scheme	scheme	NOUN
eurjchem-503	45	33	1	1	NUM
eurjchem-503	45	34	)	)	PUNCT
eurjchem-503	45	35	.	.	PUNCT
eurjchem-503	46	1	yield	yield	NOUN
eurjchem-503	46	2	:	:	PUNCT
eurjchem-503	46	3	295	295	NUM
eurjchem-503	46	4	mg	mg	NOUN
eurjchem-503	46	5	,	,	PUNCT
eurjchem-503	46	6	93	93	NUM
eurjchem-503	46	7	%	%	NOUN
eurjchem-503	46	8	.	.	PUNCT
eurjchem-503	47	1	m.p	m.p	PROPN
eurjchem-503	47	2	.	.	PROPN
eurjchem-503	47	3	:	:	PUNCT
eurjchem-503	48	1	187‐188	187‐188	NUM
eurjchem-503	48	2	oc	oc	X
eurjchem-503	48	3	.	.	PROPN
eurjchem-503	48	4	ir	ir	PROPN
eurjchem-503	48	5	(	(	PUNCT
eurjchem-503	48	6	max	max	PROPN
eurjchem-503	48	7	,	,	PUNCT
eurjchem-503	48	8	thin	thin	ADJ
eurjchem-503	48	9	film	film	NOUN
eurjchem-503	48	10	,	,	PUNCT
eurjchem-503	48	11	cm‐1	cm‐1	PROPN
eurjchem-503	48	12	):	):	PUNCT
eurjchem-503	48	13	1630	1630	NUM
eurjchem-503	48	14	(	(	PUNCT
eurjchem-503	48	15	c	c	X
eurjchem-503	48	16	=	=	SYM
eurjchem-503	48	17	c	c	NOUN
eurjchem-503	48	18	)	)	PUNCT
eurjchem-503	48	19	,	,	PUNCT
eurjchem-503	48	20	1609	1609	NUM
eurjchem-503	48	21	(	(	PUNCT
eurjchem-503	48	22	nco	nco	NOUN
eurjchem-503	48	23	)	)	PUNCT
eurjchem-503	48	24	.	.	PUNCT
eurjchem-503	49	1	1h	1h	NUM
eurjchem-503	49	2	nmr	nmr	NOUN
eurjchem-503	49	3	(	(	PUNCT
eurjchem-503	49	4	300	300	NUM
eurjchem-503	49	5	mhz	mhz	NOUN
eurjchem-503	49	6	,	,	PUNCT
eurjchem-503	49	7	cdcl3	cdcl3	NOUN
eurjchem-503	49	8	,	,	PUNCT
eurjchem-503	49	9			NUM
eurjchem-503	49	10	,	,	PUNCT
eurjchem-503	49	11	ppm	ppm	NUM
eurjchem-503	49	12	):	):	PUNCT
eurjchem-503	49	13	8.40	8.40	NUM
eurjchem-503	49	14	(	(	PUNCT
eurjchem-503	49	15	1h	1h	NUM
eurjchem-503	49	16	,	,	PUNCT
eurjchem-503	49	17	d	d	PROPN
eurjchem-503	49	18	,	,	PUNCT
eurjchem-503	49	19	j	j	PROPN
eurjchem-503	49	20	=	=	SYM
eurjchem-503	49	21	9	9	NUM
eurjchem-503	49	22	hz	hz	ADJ
eurjchem-503	49	23	,	,	PUNCT
eurjchem-503	49	24	9‐h	9‐h	NOUN
eurjchem-503	49	25	)	)	PUNCT
eurjchem-503	49	26	,	,	PUNCT
eurjchem-503	49	27	8.21(1h	8.21(1h	NUM
eurjchem-503	49	28	,	,	PUNCT
eurjchem-503	49	29	s	s	NOUN
eurjchem-503	49	30	,	,	PUNCT
eurjchem-503	49	31	n‐h	n‐h	NUM
eurjchem-503	49	32	)	)	PUNCT
eurjchem-503	49	33	,	,	PUNCT
eurjchem-503	49	34	6.62	6.62	NUM
eurjchem-503	49	35	(	(	PUNCT
eurjchem-503	49	36	1h	1h	NUM
eurjchem-503	49	37	,	,	PUNCT
eurjchem-503	49	38	m	m	PROPN
eurjchem-503	49	39	,	,	PUNCT
eurjchem-503	49	40	19‐h	19‐h	NUM
eurjchem-503	49	41	)	)	PUNCT
eurjchem-503	49	42	,	,	PUNCT
eurjchem-503	49	43	7.57‐7.42	7.57‐7.42	NUM
eurjchem-503	49	44	(	(	PUNCT
eurjchem-503	49	45	3h	3h	NUM
eurjchem-503	49	46	,	,	PUNCT
eurjchem-503	49	47	m	m	PROPN
eurjchem-503	49	48	,	,	PUNCT
eurjchem-503	49	49	16	16	NUM
eurjchem-503	49	50	,	,	PUNCT
eurjchem-503	49	51	17	17	NUM
eurjchem-503	49	52	,	,	PUNCT
eurjchem-503	49	53	and	and	CCONJ
eurjchem-503	49	54	18‐h	18‐h	NUM
eurjchem-503	49	55	)	)	PUNCT
eurjchem-503	49	56	,	,	PUNCT
eurjchem-503	49	57	6.87	6.87	NUM
eurjchem-503	49	58	(	(	PUNCT
eurjchem-503	49	59	1h	1h	NUM
eurjchem-503	49	60	,	,	PUNCT
eurjchem-503	49	61	s	s	NOUN
eurjchem-503	49	62	,	,	PUNCT
eurjchem-503	49	63	12‐h	12‐h	NUM
eurjchem-503	49	64	)	)	PUNCT
eurjchem-503	49	65	,	,	PUNCT
eurjchem-503	49	66	6.80	6.80	NUM
eurjchem-503	49	67	(	(	PUNCT
eurjchem-503	49	68	1h	1h	NUM
eurjchem-503	49	69	,	,	PUNCT
eurjchem-503	49	70	d	d	PROPN
eurjchem-503	49	71	,	,	PUNCT
eurjchem-503	49	72	j	j	PROPN
eurjchem-503	49	73	=	=	SYM
eurjchem-503	49	74	9	9	NUM
eurjchem-503	49	75	hz	hz	NOUN
eurjchem-503	49	76	,	,	PUNCT
eurjchem-503	49	77	10‐h	10‐h	NUM
eurjchem-503	49	78	)	)	PUNCT
eurjchem-503	49	79	,	,	PUNCT
eurjchem-503	49	80	6.55	6.55	NUM
eurjchem-503	49	81	(	(	PUNCT
eurjchem-503	49	82	1h	1h	NUM
eurjchem-503	49	83	,	,	PUNCT
eurjchem-503	49	84	s	s	PROPN
eurjchem-503	49	85	,	,	PUNCT
eurjchem-503	49	86	14‐h	14‐h	NUM
eurjchem-503	49	87	)	)	PUNCT
eurjchem-503	49	88	,	,	PUNCT
eurjchem-503	49	89	4.50	4.50	NUM
eurjchem-503	49	90	(	(	PUNCT
eurjchem-503	49	91	2h	2h	NUM
eurjchem-503	49	92	,	,	PUNCT
eurjchem-503	49	93	m	m	PROPN
eurjchem-503	49	94	,	,	PUNCT
eurjchem-503	49	95	5‐h2	5‐h2	NUM
eurjchem-503	49	96	)	)	PUNCT
eurjchem-503	49	97	,	,	PUNCT
eurjchem-503	49	98	3.85	3.85	NUM
eurjchem-503	49	99	(	(	PUNCT
eurjchem-503	49	100	3h	3h	NUM
eurjchem-503	49	101	,	,	PUNCT
eurjchem-503	49	102	s	s	X
eurjchem-503	49	103	,	,	PUNCT
eurjchem-503	49	104	ome	ome	PROPN
eurjchem-503	49	105	)	)	PUNCT
eurjchem-503	49	106	,	,	PUNCT
eurjchem-503	49	107	3.07	3.07	NUM
eurjchem-503	49	108	(	(	PUNCT
eurjchem-503	49	109	2h	2h	NUM
eurjchem-503	49	110	,	,	PUNCT
eurjchem-503	49	111	m	m	PROPN
eurjchem-503	49	112	,	,	PUNCT
eurjchem-503	49	113	6‐h2	6‐h2	NUM
eurjchem-503	49	114	)	)	PUNCT
eurjchem-503	49	115	.	.	PUNCT
eurjchem-503	50	1	ms	ms	NOUN
eurjchem-503	50	2	(	(	PUNCT
eurjchem-503	50	3	m	m	PROPN
eurjchem-503	50	4	/	/	SYM
eurjchem-503	50	5	z	z	NOUN
eurjchem-503	50	6	,	,	PUNCT
eurjchem-503	50	7	ei	ei	PROPN
eurjchem-503	50	8	):	):	PUNCT
eurjchem-503	50	9	316	316	NUM
eurjchem-503	50	10	.	.	PUNCT
eurjchem-503	50	11	hrms	hrm	VERB
eurjchem-503	50	12	calcd	calcd	NOUN
eurjchem-503	50	13	.	.	PUNCT
eurjchem-503	51	1	for	for	ADP
eurjchem-503	51	2	c20h16n2o2	c20h16n2o2	X
eurjchem-503	51	3	(	(	PUNCT
eurjchem-503	51	4	m+	m+	NUM
eurjchem-503	51	5	):	):	PUNCT
eurjchem-503	51	6	316.1212	316.1212	NUM
eurjchem-503	51	7	,	,	PUNCT
eurjchem-503	51	8	found	find	VERB
eurjchem-503	51	9	:	:	PUNCT
eurjchem-503	51	10	316.1214	316.1214	NUM
eurjchem-503	51	11	.	.	X
eurjchem-503	52	1	2.2.3	2.2.3	NUM
eurjchem-503	52	2	.	.	X
eurjchem-503	53	1	11‐methoxy‐16,17,19,20‐	11‐methoxy‐16,17,19,20‐	NUM
eurjchem-503	53	2	tetrahydroyohimban‐21‐one	tetrahydroyohimban‐21‐one	NOUN
eurjchem-503	53	3	(	(	PUNCT
eurjchem-503	53	4	6	6	NUM
eurjchem-503	53	5	)	)	PUNCT
eurjchem-503	53	6	the	the	DET
eurjchem-503	53	7	title	title	NOUN
eurjchem-503	53	8	compound	compound	NOUN
eurjchem-503	53	9	6	6	NUM
eurjchem-503	53	10	was	be	AUX
eurjchem-503	53	11	synthesized	synthesize	VERB
eurjchem-503	53	12	following	follow	VERB
eurjchem-503	53	13	the	the	DET
eurjchem-503	53	14	above	above	ADJ
eurjchem-503	53	15	procedure	procedure	NOUN
eurjchem-503	53	16	used	use	VERB
eurjchem-503	53	17	for	for	ADP
eurjchem-503	53	18	compound	compound	NOUN
eurjchem-503	53	19	5	5	NUM
eurjchem-503	53	20	except	except	SCONJ
eurjchem-503	53	21	irradiation	irradiation	NOUN
eurjchem-503	53	22	time	time	NOUN
eurjchem-503	53	23	was	be	AUX
eurjchem-503	53	24	1	1	NUM
eurjchem-503	53	25	hour	hour	NOUN
eurjchem-503	53	26	instead	instead	ADV
eurjchem-503	53	27	of	of	ADP
eurjchem-503	53	28	6	6	NUM
eurjchem-503	53	29	hours	hour	NOUN
eurjchem-503	53	30	(	(	PUNCT
eurjchem-503	53	31	starting	start	VERB
eurjchem-503	53	32	enamide	enamide	NOUN
eurjchem-503	53	33	disappeared	disappear	VERB
eurjchem-503	53	34	on	on	ADP
eurjchem-503	53	35	tlc	tlc	PROPN
eurjchem-503	53	36	)	)	PUNCT
eurjchem-503	53	37	,	,	PUNCT
eurjchem-503	53	38	lactam	lactam	NOUN
eurjchem-503	53	39	6	6	NUM
eurjchem-503	53	40	was	be	AUX
eurjchem-503	53	41	obtained	obtain	VERB
eurjchem-503	53	42	as	as	ADP
eurjchem-503	53	43	light	light	ADJ
eurjchem-503	53	44	yellow	yellow	ADJ
eurjchem-503	53	45	crystals	crystal	NOUN
eurjchem-503	53	46	(	(	PUNCT
eurjchem-503	53	47	scheme	scheme	NOUN
eurjchem-503	53	48	1	1	NUM
eurjchem-503	53	49	)	)	PUNCT
eurjchem-503	53	50	.	.	PUNCT
eurjchem-503	54	1	m.p	m.p	PROPN
eurjchem-503	54	2	.	.	PROPN
eurjchem-503	54	3	:	:	PUNCT
eurjchem-503	55	1	247‐249	247‐249	PROPN
eurjchem-503	55	2	oc	oc	PROPN
eurjchem-503	55	3	.	.	PROPN
eurjchem-503	55	4	yield	yield	NOUN
eurjchem-503	55	5	:	:	PUNCT
eurjchem-503	55	6	290	290	NUM
eurjchem-503	55	7	mg	mg	NUM
eurjchem-503	55	8	,	,	PUNCT
eurjchem-503	55	9	93	93	NUM
eurjchem-503	55	10	%	%	NOUN
eurjchem-503	55	11	.	.	PUNCT
eurjchem-503	56	1	ir	ir	PROPN
eurjchem-503	56	2	(	(	PUNCT
eurjchem-503	56	3	max	max	PROPN
eurjchem-503	56	4	,	,	PUNCT
eurjchem-503	56	5	thin	thin	ADJ
eurjchem-503	56	6	film	film	NOUN
eurjchem-503	56	7	,	,	PUNCT
eurjchem-503	56	8	cm‐1	cm‐1	PROPN
eurjchem-503	56	9	):	):	PUNCT
eurjchem-503	56	10	3316	3316	NUM
eurjchem-503	56	11	(	(	PUNCT
eurjchem-503	56	12	nh	nh	NOUN
eurjchem-503	56	13	)	)	PUNCT
eurjchem-503	56	14	,	,	PUNCT
eurjchem-503	56	15	1682	1682	NUM
eurjchem-503	56	16	and	and	CCONJ
eurjchem-503	56	17	1632	1632	NUM
eurjchem-503	56	18	(	(	PUNCT
eurjchem-503	56	19	c	c	NOUN
eurjchem-503	56	20	=	=	SYM
eurjchem-503	56	21	c	c	NOUN
eurjchem-503	56	22	)	)	PUNCT
eurjchem-503	56	23	,	,	PUNCT
eurjchem-503	56	24	1592	1592	NUM
eurjchem-503	56	25	(	(	PUNCT
eurjchem-503	56	26	nco	nco	NOUN
eurjchem-503	56	27	)	)	PUNCT
eurjchem-503	56	28	.	.	PUNCT
eurjchem-503	57	1	1h	1h	NUM
eurjchem-503	57	2	nmr	nmr	NOUN
eurjchem-503	57	3	(	(	PUNCT
eurjchem-503	57	4	400	400	NUM
eurjchem-503	57	5	mhz	mhz	NOUN
eurjchem-503	57	6	,	,	PUNCT
eurjchem-503	57	7	cdcl3	cdcl3	NOUN
eurjchem-503	57	8	,	,	PUNCT
eurjchem-503	57	9			NUM
eurjchem-503	57	10	,	,	PUNCT
eurjchem-503	57	11	ppm	ppm	NUM
eurjchem-503	57	12	):	):	PUNCT
eurjchem-503	57	13	10.8	10.8	NUM
eurjchem-503	57	14	(	(	PUNCT
eurjchem-503	57	15	1h	1h	NUM
eurjchem-503	57	16	,	,	PUNCT
eurjchem-503	57	17	s	s	X
eurjchem-503	57	18	,	,	PUNCT
eurjchem-503	57	19	nh	nh	PROPN
eurjchem-503	57	20	)	)	PUNCT
eurjchem-503	57	21	,	,	PUNCT
eurjchem-503	57	22	7.26	7.26	NUM
eurjchem-503	57	23	(	(	PUNCT
eurjchem-503	57	24	1h	1h	NUM
eurjchem-503	57	25	,	,	PUNCT
eurjchem-503	57	26	d	d	PROPN
eurjchem-503	57	27	,	,	PUNCT
eurjchem-503	57	28	j	j	PROPN
eurjchem-503	57	29	=	=	SYM
eurjchem-503	57	30	8.5	8.5	NUM
eurjchem-503	57	31	hz	hz	NOUN
eurjchem-503	57	32	,	,	PUNCT
eurjchem-503	57	33	9‐h	9‐h	NOUN
eurjchem-503	57	34	)	)	PUNCT
eurjchem-503	57	35	,	,	PUNCT
eurjchem-503	57	36	6.81	6.81	NUM
eurjchem-503	57	37	(	(	PUNCT
eurjchem-503	57	38	1h	1h	NUM
eurjchem-503	57	39	,	,	PUNCT
eurjchem-503	57	40	d	d	PROPN
eurjchem-503	57	41	,	,	PUNCT
eurjchem-503	57	42	j	j	PROPN
eurjchem-503	58	1	=	=	SYM
eurjchem-503	58	2	8.5	8.5	NUM
eurjchem-503	58	3	hz	hz	NOUN
eurjchem-503	58	4	,	,	PUNCT
eurjchem-503	58	5	10‐h	10‐h	NUM
eurjchem-503	58	6	)	)	PUNCT
eurjchem-503	58	7	,	,	PUNCT
eurjchem-503	58	8	6.73	6.73	NUM
eurjchem-503	58	9	(	(	PUNCT
eurjchem-503	58	10	1h	1h	NUM
eurjchem-503	58	11	,	,	PUNCT
eurjchem-503	58	12	br	br	PROPN
eurjchem-503	58	13	s	s	PROPN
eurjchem-503	58	14	,	,	PUNCT
eurjchem-503	58	15	12‐h	12‐h	NUM
eurjchem-503	58	16	)	)	PUNCT
eurjchem-503	58	17	,	,	PUNCT
eurjchem-503	58	18	6.62	6.62	NUM
eurjchem-503	58	19	(	(	PUNCT
eurjchem-503	58	20	1h	1h	NUM
eurjchem-503	58	21	,	,	PUNCT
eurjchem-503	58	22	m	m	PROPN
eurjchem-503	58	23	,	,	PUNCT
eurjchem-503	58	24	19‐h	19‐h	NUM
eurjchem-503	58	25	)	)	PUNCT
eurjchem-503	58	26	,	,	PUNCT
eurjchem-503	58	27	5.72	5.72	NUM
eurjchem-503	58	28	(	(	PUNCT
eurjchem-503	58	29	1h	1h	NUM
eurjchem-503	58	30	,	,	PUNCT
eurjchem-503	58	31	m	m	PROPN
eurjchem-503	58	32	,	,	PUNCT
eurjchem-503	58	33	16‐h	16‐h	NUM
eurjchem-503	58	34	)	)	PUNCT
eurjchem-503	58	35	,	,	PUNCT
eurjchem-503	58	36	5.36	5.36	NUM
eurjchem-503	58	37	(	(	PUNCT
eurjchem-503	58	38	1h	1h	NUM
eurjchem-503	58	39	,	,	PUNCT
eurjchem-503	58	40	m	m	PROPN
eurjchem-503	58	41	,	,	PUNCT
eurjchem-503	58	42	17‐h	17‐h	NUM
eurjchem-503	58	43	)	)	PUNCT
eurjchem-503	58	44	,	,	PUNCT
eurjchem-503	58	45	4.82	4.82	NUM
eurjchem-503	58	46	(	(	PUNCT
eurjchem-503	58	47	1h	1h	NUM
eurjchem-503	58	48	,	,	PUNCT
eurjchem-503	58	49	brdd	brdd	NOUN
eurjchem-503	58	50	,	,	PUNCT
eurjchem-503	58	51	j	j	NOUN
eurjchem-503	58	52	=	=	SYM
eurjchem-503	58	53	12	12	NUM
eurjchem-503	58	54	and	and	CCONJ
eurjchem-503	58	55	4	4	NUM
eurjchem-503	58	56	hz	hz	NOUN
eurjchem-503	58	57	,	,	PUNCT
eurjchem-503	58	58	3‐h	3‐h	NUM
eurjchem-503	58	59	)	)	PUNCT
eurjchem-503	58	60	,	,	PUNCT
eurjchem-503	58	61	3.73	3.73	NUM
eurjchem-503	58	62	(	(	PUNCT
eurjchem-503	58	63	3h	3h	NUM
eurjchem-503	58	64	,	,	PUNCT
eurjchem-503	58	65	s	s	X
eurjchem-503	58	66	,	,	PUNCT
eurjchem-503	58	67	och3	och3	ADJ
eurjchem-503	58	68	)	)	PUNCT
eurjchem-503	58	69	,	,	PUNCT
eurjchem-503	58	70	3.15	3.15	NUM
eurjchem-503	58	71	(	(	PUNCT
eurjchem-503	58	72	1h	1h	NUM
eurjchem-503	58	73	,	,	PUNCT
eurjchem-503	58	74	m	m	PROPN
eurjchem-503	58	75	,	,	PUNCT
eurjchem-503	58	76	15‐h	15‐h	NUM
eurjchem-503	58	77	)	)	PUNCT
eurjchem-503	58	78	,	,	PUNCT
eurjchem-503	58	79	2.89‐2.70	2.89‐2.70	NUM
eurjchem-503	58	80	(	(	PUNCT
eurjchem-503	58	81	6h	6h	NUM
eurjchem-503	58	82	,	,	PUNCT
eurjchem-503	58	83	m	m	PROPN
eurjchem-503	58	84	,	,	PUNCT
eurjchem-503	58	85	18‐h2	18‐h2	PROPN
eurjchem-503	58	86	,	,	PUNCT
eurjchem-503	58	87	6‐h2	6‐h2	NUM
eurjchem-503	58	88	,	,	PUNCT
eurjchem-503	58	89	and	and	CCONJ
eurjchem-503	58	90	5‐h2	5‐h2	NUM
eurjchem-503	58	91	)	)	PUNCT
eurjchem-503	58	92	,	,	PUNCT
eurjchem-503	58	93	2.58	2.58	NUM
eurjchem-503	58	94	(	(	PUNCT
eurjchem-503	58	95	1h	1h	NUM
eurjchem-503	58	96	,	,	PUNCT
eurjchem-503	58	97	ddd	ddd	PROPN
eurjchem-503	58	98	,	,	PUNCT
eurjchem-503	58	99	j	j	NOUN
eurjchem-503	58	100	=	=	SYM
eurjchem-503	58	101	12	12	NUM
eurjchem-503	58	102	,	,	PUNCT
eurjchem-503	58	103	4	4	NUM
eurjchem-503	58	104	,	,	PUNCT
eurjchem-503	58	105	and	and	CCONJ
eurjchem-503	58	106	3.5	3.5	NUM
eurjchem-503	58	107	hz	hz	NOUN
eurjchem-503	58	108	,	,	PUNCT
eurjchem-503	58	109	14‐heq	14‐heq	NUM
eurjchem-503	58	110	)	)	PUNCT
eurjchem-503	58	111	,	,	PUNCT
eurjchem-503	58	112	1.32	1.32	NUM
eurjchem-503	58	113	(	(	PUNCT
eurjchem-503	58	114	1h	1h	NUM
eurjchem-503	58	115	,	,	PUNCT
eurjchem-503	58	116	q	q	NOUN
eurjchem-503	58	117	,	,	PUNCT
eurjchem-503	58	118	j	j	PROPN
eurjchem-503	59	1	=	=	PROPN
eurjchem-503	59	2	12	12	NUM
eurjchem-503	59	3	hz	hz	VERB
eurjchem-503	59	4	,	,	PUNCT
eurjchem-503	59	5	14‐hax	14‐hax	NUM
eurjchem-503	59	6	)	)	PUNCT
eurjchem-503	59	7	.	.	PUNCT
eurjchem-503	60	1	ms	ms	NOUN
eurjchem-503	60	2	(	(	PUNCT
eurjchem-503	60	3	m	m	PROPN
eurjchem-503	60	4	/	/	SYM
eurjchem-503	60	5	z	z	NOUN
eurjchem-503	60	6	,	,	PUNCT
eurjchem-503	60	7	ei	ei	PROPN
eurjchem-503	60	8	):	):	PUNCT
eurjchem-503	60	9	320	320	NUM
eurjchem-503	60	10	;	;	PUNCT
eurjchem-503	60	11	hrms	hrm	VERB
eurjchem-503	60	12	calcd	calcd	NOUN
eurjchem-503	60	13	.	.	PUNCT
eurjchem-503	61	1	for	for	ADP
eurjchem-503	61	2	c20h20n2o2	c20h20n2o2	NOUN
eurjchem-503	61	3	(	(	PUNCT
eurjchem-503	61	4	m+	m+	NOUN
eurjchem-503	61	5	)	)	PUNCT
eurjchem-503	61	6	320.1525	320.1525	NUM
eurjchem-503	61	7	,	,	PUNCT
eurjchem-503	61	8	found	find	VERB
eurjchem-503	61	9	:	:	PUNCT
eurjchem-503	61	10	320.1521	320.1521	NUM
eurjchem-503	61	11	.	.	NOUN
eurjchem-503	62	1	2.2.4	2.2.4	NUM
eurjchem-503	62	2	.	.	NOUN
eurjchem-503	62	3	11‐methoxy‐2,3,4,9‐tetrahydro‐2‐(4‐methoxybenzoyl)‐	11‐methoxy‐2,3,4,9‐tetrahydro‐2‐(4‐methoxybenzoyl)‐	NUM
eurjchem-503	62	4	1‐methylen‐1h‐pyrido[3,4]‐indole	1‐methylen‐1h‐pyrido[3,4]‐indole	PROPN
eurjchem-503	62	5	(	(	PUNCT
eurjchem-503	62	6	8)	8)	NUM
eurjchem-503	62	7	4‐methoxybenzoyl	4‐methoxybenzoyl	ADJ
eurjchem-503	62	8	chloride	chloride	NOUN
eurjchem-503	62	9	(	(	PUNCT
eurjchem-503	62	10	450	450	NUM
eurjchem-503	62	11	mg	mg	NOUN
eurjchem-503	62	12	,	,	PUNCT
eurjchem-503	62	13	2.64	2.64	NUM
eurjchem-503	62	14	mmol	mmol	NOUN
eurjchem-503	62	15	)	)	PUNCT
eurjchem-503	62	16	was	be	AUX
eurjchem-503	62	17	added	add	VERB
eurjchem-503	62	18	dropwise	dropwise	NOUN
eurjchem-503	62	19	to	to	ADP
eurjchem-503	62	20	ice‐cooled	ice‐coole	VERB
eurjchem-503	62	21	,	,	PUNCT
eurjchem-503	62	22	stirred	stir	VERB
eurjchem-503	62	23	solution	solution	NOUN
eurjchem-503	62	24	of	of	ADP
eurjchem-503	62	25	harmaline	harmaline	NOUN
eurjchem-503	62	26	,	,	PUNCT
eurjchem-503	62	27	2	2	NUM
eurjchem-503	62	28	,	,	PUNCT
eurjchem-503	62	29	(	(	PUNCT
eurjchem-503	62	30	220	220	NUM
eurjchem-503	62	31	mg	mg	NOUN
eurjchem-503	62	32	,	,	PUNCT
eurjchem-503	62	33	1.03	1.03	NUM
eurjchem-503	62	34	mmol	mmol	NOUN
eurjchem-503	62	35	)	)	PUNCT
eurjchem-503	62	36	and	and	CCONJ
eurjchem-503	62	37	triethylamine	triethylamine	NOUN
eurjchem-503	62	38	(	(	PUNCT
eurjchem-503	62	39	600	600	NUM
eurjchem-503	62	40	mg	mg	PROPN
eurjchem-503	62	41	,	,	PUNCT
eurjchem-503	62	42	5.93	5.93	NUM
eurjchem-503	62	43	mmol	mmol	NOUN
eurjchem-503	62	44	)	)	PUNCT
eurjchem-503	62	45	in	in	ADP
eurjchem-503	62	46	anhydrous	anhydrous	ADJ
eurjchem-503	62	47	benzene	benzene	NOUN
eurjchem-503	62	48	(	(	PUNCT
eurjchem-503	62	49	70	70	NUM
eurjchem-503	62	50	ml	ml	NOUN
eurjchem-503	62	51	)	)	PUNCT
eurjchem-503	62	52	.	.	PUNCT
eurjchem-503	63	1	after	after	ADP
eurjchem-503	63	2	being	be	AUX
eurjchem-503	63	3	stirred	stir	VERB
eurjchem-503	63	4	at	at	ADP
eurjchem-503	63	5	room	room	NOUN
eurjchem-503	63	6	temperature	temperature	NOUN
eurjchem-503	63	7	for	for	ADP
eurjchem-503	63	8	45	45	NUM
eurjchem-503	63	9	minutes	minute	NOUN
eurjchem-503	63	10	,	,	PUNCT
eurjchem-503	63	11	the	the	DET
eurjchem-503	63	12	reaction	reaction	NOUN
eurjchem-503	63	13	mixture	mixture	NOUN
eurjchem-503	63	14	was	be	AUX
eurjchem-503	63	15	filtered	filter	VERB
eurjchem-503	63	16	to	to	PART
eurjchem-503	63	17	remove	remove	VERB
eurjchem-503	63	18	triethylamine	triethylamine	NOUN
eurjchem-503	63	19	hydrochloride	hydrochloride	NOUN
eurjchem-503	63	20	.	.	PUNCT
eurjchem-503	64	1	the	the	DET
eurjchem-503	64	2	filtrate	filtrate	NOUN
eurjchem-503	64	3	was	be	AUX
eurjchem-503	64	4	evaporated	evaporate	VERB
eurjchem-503	64	5	to	to	PART
eurjchem-503	64	6	give	give	VERB
eurjchem-503	64	7	the	the	DET
eurjchem-503	64	8	unstable	unstable	ADJ
eurjchem-503	64	9	enamide	enamide	NOUN
eurjchem-503	64	10	,	,	PUNCT
eurjchem-503	64	11	8	8	NUM
eurjchem-503	64	12	,	,	PUNCT
eurjchem-503	64	13	(	(	PUNCT
eurjchem-503	64	14	350	350	NUM
eurjchem-503	64	15	mg	mg	NOUN
eurjchem-503	64	16	,	,	PUNCT
eurjchem-503	64	17	98	98	NUM
eurjchem-503	64	18	%	%	NOUN
eurjchem-503	64	19	)	)	PUNCT
eurjchem-503	64	20	as	as	ADP
eurjchem-503	64	21	a	a	DET
eurjchem-503	64	22	brown	brown	ADJ
eurjchem-503	64	23	gum	gum	NOUN
eurjchem-503	64	24	,	,	PUNCT
eurjchem-503	64	25	which	which	PRON
eurjchem-503	64	26	was	be	AUX
eurjchem-503	64	27	used	use	VERB
eurjchem-503	64	28	for	for	ADP
eurjchem-503	64	29	irradiation	irradiation	NOUN
eurjchem-503	64	30	without	without	ADP
eurjchem-503	64	31	further	further	ADJ
eurjchem-503	64	32	purification	purification	NOUN
eurjchem-503	64	33	(	(	PUNCT
eurjchem-503	64	34	scheme	scheme	NOUN
eurjchem-503	64	35	2	2	NUM
eurjchem-503	64	36	)	)	PUNCT
eurjchem-503	64	37	.	.	PUNCT
eurjchem-503	65	1	2.2.5	2.2.5	NUM
eurjchem-503	65	2	.	.	X
eurjchem-503	65	3	11,17‐dimethoxy‐16,17,19,20‐tetrahydroxy‐	11,17‐dimethoxy‐16,17,19,20‐tetrahydroxy‐	NUM
eurjchem-503	65	4	yohimban‐21‐one	yohimban‐21‐one	NOUN
eurjchem-503	65	5	(	(	PUNCT
eurjchem-503	65	6	9	9	NUM
eurjchem-503	65	7	)	)	PUNCT
eurjchem-503	65	8	sodium	sodium	NOUN
eurjchem-503	65	9	borohydride	borohydride	NOUN
eurjchem-503	65	10	(	(	PUNCT
eurjchem-503	65	11	525	525	NUM
eurjchem-503	65	12	mg	mg	PROPN
eurjchem-503	65	13	,	,	PUNCT
eurjchem-503	65	14	13.9	13.9	NUM
eurjchem-503	65	15	mmol	mmol	NOUN
eurjchem-503	65	16	)	)	PUNCT
eurjchem-503	65	17	and	and	CCONJ
eurjchem-503	65	18	methanol	methanol	NOUN
eurjchem-503	65	19	(	(	PUNCT
eurjchem-503	65	20	50	50	NUM
eurjchem-503	65	21	ml	ml	NOUN
eurjchem-503	65	22	)	)	PUNCT
eurjchem-503	65	23	were	be	AUX
eurjchem-503	65	24	added	add	VERB
eurjchem-503	65	25	successively	successively	ADV
eurjchem-503	65	26	to	to	ADP
eurjchem-503	65	27	a	a	DET
eurjchem-503	65	28	stirred	stir	VERB
eurjchem-503	65	29	solution	solution	NOUN
eurjchem-503	65	30	of	of	ADP
eurjchem-503	65	31	the	the	DET
eurjchem-503	65	32	enamide	enamide	NOUN
eurjchem-503	65	33	,	,	PUNCT
eurjchem-503	65	34	8	8	NUM
eurjchem-503	65	35	,	,	PUNCT
eurjchem-503	65	36	(	(	PUNCT
eurjchem-503	65	37	350	350	NUM
eurjchem-503	65	38	mg	mg	NOUN
eurjchem-503	65	39	,	,	PUNCT
eurjchem-503	65	40	1.00	1.00	NUM
eurjchem-503	65	41	mmol	mmol	NOUN
eurjchem-503	65	42	)	)	PUNCT
eurjchem-503	65	43	in	in	ADP
eurjchem-503	65	44	acetonitrile	acetonitrile	NOUN
eurjchem-503	65	45	(	(	PUNCT
eurjchem-503	65	46	150	150	NUM
eurjchem-503	65	47	ml	ml	NOUN
eurjchem-503	65	48	)	)	PUNCT
eurjchem-503	65	49	at	at	ADP
eurjchem-503	65	50	room	room	NOUN
eurjchem-503	65	51	temperature	temperature	NOUN
eurjchem-503	65	52	and	and	CCONJ
eurjchem-503	65	53	resulting	result	VERB
eurjchem-503	65	54	solution	solution	NOUN
eurjchem-503	65	55	was	be	AUX
eurjchem-503	65	56	cooled	cool	VERB
eurjchem-503	65	57	to	to	ADP
eurjchem-503	65	58	‐5	‐5	PROPN
eurjchem-503	65	59	oc	oc	NOUN
eurjchem-503	65	60	and	and	CCONJ
eurjchem-503	65	61	irradiated	irradiate	VERB
eurjchem-503	65	62	for	for	ADP
eurjchem-503	65	63	1	1	NUM
eurjchem-503	65	64	hour	hour	NOUN
eurjchem-503	65	65	(	(	PUNCT
eurjchem-503	65	66	starting	start	VERB
eurjchem-503	65	67	enamide	enamide	NOUN
eurjchem-503	65	68	disappeared	disappear	VERB
eurjchem-503	65	69	on	on	ADP
eurjchem-503	65	70	tlc	tlc	PROPN
eurjchem-503	65	71	)	)	PUNCT
eurjchem-503	65	72	.	.	PUNCT
eurjchem-503	66	1	the	the	DET
eurjchem-503	66	2	reaction	reaction	NOUN
eurjchem-503	66	3	mixture	mixture	NOUN
eurjchem-503	66	4	was	be	AUX
eurjchem-503	66	5	filtered	filter	VERB
eurjchem-503	66	6	and	and	CCONJ
eurjchem-503	66	7	evaporated	evaporate	VERB
eurjchem-503	66	8	under	under	ADP
eurjchem-503	66	9	reduced	reduced	ADJ
eurjchem-503	66	10	pressure	pressure	NOUN
eurjchem-503	66	11	.	.	PUNCT
eurjchem-503	67	1	10	10	NUM
eurjchem-503	67	2	%	%	NOUN
eurjchem-503	67	3	sodium	sodium	NOUN
eurjchem-503	67	4	bicarbonate	bicarbonate	NOUN
eurjchem-503	67	5	was	be	AUX
eurjchem-503	67	6	added	add	VERB
eurjchem-503	67	7	,	,	PUNCT
eurjchem-503	67	8	shaken	shake	VERB
eurjchem-503	67	9	well	well	ADV
eurjchem-503	67	10	and	and	CCONJ
eurjchem-503	67	11	extracted	extract	VERB
eurjchem-503	67	12	with	with	ADP
eurjchem-503	67	13	ethyl	ethyl	PROPN
eurjchem-503	67	14	acetate	acetate	NOUN
eurjchem-503	67	15	.	.	PUNCT
eurjchem-503	68	1	28	28	NUM
eurjchem-503	68	2	yar	yar	PROPN
eurjchem-503	68	3	et	et	PROPN
eurjchem-503	68	4	al	al	PROPN
eurjchem-503	68	5	.	.	PUNCT
eurjchem-503	68	6	/	/	SYM
eurjchem-503	68	7	european	european	PROPN
eurjchem-503	68	8	journal	journal	PROPN
eurjchem-503	68	9	of	of	ADP
eurjchem-503	68	10	chemistry	chemistry	NOUN
eurjchem-503	68	11	3	3	NUM
eurjchem-503	68	12	(	(	PUNCT
eurjchem-503	68	13	1	1	NUM
eurjchem-503	68	14	)	)	PUNCT
eurjchem-503	68	15	(	(	PUNCT
eurjchem-503	68	16	2012	2012	NUM
eurjchem-503	68	17	)	)	PUNCT
eurjchem-503	68	18	26‐31	26‐31	ADV
eurjchem-503	68	19	a	a	X
eurjchem-503	68	20	)	)	PUNCT
eurjchem-503	68	21	et3n	et3n	PROPN
eurjchem-503	68	22	(	(	PUNCT
eurjchem-503	68	23	6	6	NUM
eurjchem-503	68	24	eq	eq	NOUN
eurjchem-503	68	25	.	.	PROPN
eurjchem-503	68	26	)	)	PUNCT
eurjchem-503	68	27	,	,	PUNCT
eurjchem-503	68	28	anhydrous	anhydrous	ADJ
eurjchem-503	68	29	benzene	benzene	NOUN
eurjchem-503	68	30	,	,	PUNCT
eurjchem-503	68	31	0	0	NUM
eurjchem-503	68	32	-	-	SYM
eurjchem-503	68	33	5	5	NUM
eurjchem-503	68	34	oc	oc	NOUN
eurjchem-503	68	35	,	,	PUNCT
eurjchem-503	68	36	30	30	NUM
eurjchem-503	68	37	min	min	NOUN
eurjchem-503	68	38	.	.	PROPN
eurjchem-503	68	39	,	,	PUNCT
eurjchem-503	68	40	97	97	NUM
eurjchem-503	68	41	%	%	NOUN
eurjchem-503	68	42	.	.	PUNCT
eurjchem-503	69	1	b	b	X
eurjchem-503	69	2	)	)	PUNCT
eurjchem-503	69	3	nabh4	nabh4	NOUN
eurjchem-503	69	4	(	(	PUNCT
eurjchem-503	69	5	9	9	NUM
eurjchem-503	69	6	eq	eq	NOUN
eurjchem-503	69	7	.	.	PROPN
eurjchem-503	69	8	)	)	PUNCT
eurjchem-503	69	9	,	,	PUNCT
eurjchem-503	69	10	ch3cn	ch3cn	PROPN
eurjchem-503	69	11	:	:	PUNCT
eurjchem-503	69	12	meoh	meoh	PROPN
eurjchem-503	69	13	(	(	PUNCT
eurjchem-503	69	14	9:1	9:1	NUM
eurjchem-503	69	15	)	)	PUNCT
eurjchem-503	69	16	,	,	PUNCT
eurjchem-503	69	17	0	0	NUM
eurjchem-503	69	18	-	-	SYM
eurjchem-503	69	19	5	5	NUM
eurjchem-503	69	20	oc	oc	NOUN
eurjchem-503	69	21	,	,	PUNCT
eurjchem-503	69	22	irradiation	irradiation	NOUN
eurjchem-503	69	23	using	use	VERB
eurjchem-503	69	24	high	high	ADJ
eurjchem-503	69	25	pressure	pressure	NOUN
eurjchem-503	69	26	mercury	mercury	NOUN
eurjchem-503	69	27	lamp	lamp	NOUN
eurjchem-503	69	28	,	,	PUNCT
eurjchem-503	69	29	6	6	NUM
eurjchem-503	69	30	h	h	NOUN
eurjchem-503	69	31	,	,	PUNCT
eurjchem-503	69	32	92	92	NUM
eurjchem-503	69	33	%	%	NOUN
eurjchem-503	69	34	.	.	PUNCT
eurjchem-503	70	1	c	c	X
eurjchem-503	70	2	)	)	PUNCT
eurjchem-503	70	3	nabh4	nabh4	NOUN
eurjchem-503	70	4	(	(	PUNCT
eurjchem-503	70	5	9	9	NUM
eurjchem-503	70	6	eq	eq	NOUN
eurjchem-503	70	7	.	.	PROPN
eurjchem-503	70	8	)	)	PUNCT
eurjchem-503	70	9	,	,	PUNCT
eurjchem-503	70	10	ch3cn	ch3cn	PROPN
eurjchem-503	70	11	:	:	PUNCT
eurjchem-503	70	12	meoh	meoh	PROPN
eurjchem-503	70	13	(	(	PUNCT
eurjchem-503	70	14	9:1	9:1	NUM
eurjchem-503	70	15	)	)	PUNCT
eurjchem-503	70	16	,	,	PUNCT
eurjchem-503	70	17	0	0	NUM
eurjchem-503	70	18	-	-	SYM
eurjchem-503	70	19	5	5	NUM
eurjchem-503	70	20	oc	oc	NOUN
eurjchem-503	70	21	,	,	PUNCT
eurjchem-503	70	22	irradiation	irradiation	NOUN
eurjchem-503	70	23	using	use	VERB
eurjchem-503	70	24	high	high	ADJ
eurjchem-503	70	25	pressure	pressure	NOUN
eurjchem-503	70	26	mercury	mercury	NOUN
eurjchem-503	70	27	lamp	lamp	NOUN
eurjchem-503	70	28	,	,	PUNCT
eurjchem-503	70	29	1	1	NUM
eurjchem-503	70	30	h	h	NOUN
eurjchem-503	70	31	,	,	PUNCT
eurjchem-503	70	32	90	90	NUM
eurjchem-503	70	33	%	%	NOUN
eurjchem-503	70	34	.	.	PUNCT
eurjchem-503	71	1	scheme	scheme	NOUN
eurjchem-503	71	2	1	1	NUM
eurjchem-503	71	3	a	a	NOUN
eurjchem-503	71	4	)	)	PUNCT
eurjchem-503	71	5	et3n	et3n	PROPN
eurjchem-503	72	1	(	(	PUNCT
eurjchem-503	72	2	5	5	NUM
eurjchem-503	72	3	eq	eq	NOUN
eurjchem-503	72	4	.	.	PROPN
eurjchem-503	72	5	)	)	PUNCT
eurjchem-503	73	1	,	,	PUNCT
eurjchem-503	73	2	anhydrous	anhydrous	ADJ
eurjchem-503	73	3	benzene	benzene	NOUN
eurjchem-503	73	4	,	,	PUNCT
eurjchem-503	73	5	0	0	NUM
eurjchem-503	73	6	-	-	SYM
eurjchem-503	73	7	5	5	NUM
eurjchem-503	73	8	oc	oc	NOUN
eurjchem-503	73	9	,	,	PUNCT
eurjchem-503	73	10	30	30	NUM
eurjchem-503	73	11	min	min	NOUN
eurjchem-503	73	12	.	.	PROPN
eurjchem-503	73	13	,	,	PUNCT
eurjchem-503	73	14	98	98	NUM
eurjchem-503	73	15	%	%	NOUN
eurjchem-503	73	16	.	.	PUNCT
eurjchem-503	74	1	b	b	X
eurjchem-503	74	2	)	)	PUNCT
eurjchem-503	74	3	nabh4	nabh4	NOUN
eurjchem-503	74	4	(	(	PUNCT
eurjchem-503	74	5	14	14	NUM
eurjchem-503	74	6	eq	eq	NOUN
eurjchem-503	74	7	.	.	PROPN
eurjchem-503	74	8	)	)	PUNCT
eurjchem-503	74	9	,	,	PUNCT
eurjchem-503	74	10	ch3cn	ch3cn	PROPN
eurjchem-503	74	11	:	:	PUNCT
eurjchem-503	74	12	meoh	meoh	PROPN
eurjchem-503	74	13	(	(	PUNCT
eurjchem-503	74	14	9:1	9:1	NUM
eurjchem-503	74	15	)	)	PUNCT
eurjchem-503	74	16	,	,	PUNCT
eurjchem-503	74	17	0	0	NUM
eurjchem-503	74	18	-	-	SYM
eurjchem-503	74	19	5	5	NUM
eurjchem-503	74	20	oc	oc	NOUN
eurjchem-503	74	21	,	,	PUNCT
eurjchem-503	74	22	irradiation	irradiation	NOUN
eurjchem-503	74	23	using	use	VERB
eurjchem-503	74	24	high	high	ADJ
eurjchem-503	74	25	pressure	pressure	NOUN
eurjchem-503	74	26	mercury	mercury	NOUN
eurjchem-503	74	27	lamp	lamp	NOUN
eurjchem-503	74	28	,	,	PUNCT
eurjchem-503	74	29	1	1	NUM
eurjchem-503	74	30	h	h	NOUN
eurjchem-503	74	31	,	,	PUNCT
eurjchem-503	74	32	98	98	NUM
eurjchem-503	74	33	%	%	NOUN
eurjchem-503	74	34	.	.	PUNCT
eurjchem-503	75	1	scheme	scheme	NOUN
eurjchem-503	75	2	2	2	NUM
eurjchem-503	75	3	the	the	DET
eurjchem-503	75	4	organic	organic	ADJ
eurjchem-503	75	5	layer	layer	NOUN
eurjchem-503	75	6	was	be	AUX
eurjchem-503	75	7	dried	dry	VERB
eurjchem-503	75	8	over	over	ADP
eurjchem-503	75	9	sodium	sodium	NOUN
eurjchem-503	75	10	sulfate	sulfate	NOUN
eurjchem-503	75	11	and	and	CCONJ
eurjchem-503	75	12	evaporated	evaporate	VERB
eurjchem-503	75	13	to	to	PART
eurjchem-503	75	14	give	give	VERB
eurjchem-503	75	15	a	a	DET
eurjchem-503	75	16	solid	solid	NOUN
eurjchem-503	75	17	,	,	PUNCT
eurjchem-503	75	18	which	which	PRON
eurjchem-503	75	19	was	be	AUX
eurjchem-503	75	20	recrystallized	recrystallize	VERB
eurjchem-503	75	21	from	from	ADP
eurjchem-503	75	22	methanol	methanol	NOUN
eurjchem-503	75	23	to	to	PART
eurjchem-503	75	24	give	give	VERB
eurjchem-503	75	25	a	a	DET
eurjchem-503	75	26	lactam	lactam	NOUN
eurjchem-503	75	27	,	,	PUNCT
eurjchem-503	75	28	9	9	NUM
eurjchem-503	75	29	,	,	PUNCT
eurjchem-503	75	30	as	as	ADP
eurjchem-503	75	31	light	light	ADJ
eurjchem-503	75	32	yellow	yellow	ADJ
eurjchem-503	75	33	crystals	crystal	NOUN
eurjchem-503	75	34	(	(	PUNCT
eurjchem-503	75	35	scheme	scheme	NOUN
eurjchem-503	75	36	2	2	NUM
eurjchem-503	75	37	)	)	PUNCT
eurjchem-503	75	38	.	.	PUNCT
eurjchem-503	76	1	yield	yield	NOUN
eurjchem-503	76	2	:	:	PUNCT
eurjchem-503	76	3	342	342	NUM
eurjchem-503	76	4	mg	mg	NOUN
eurjchem-503	76	5	,	,	PUNCT
eurjchem-503	76	6	98	98	NUM
eurjchem-503	76	7	%	%	NOUN
eurjchem-503	76	8	.	.	PUNCT
eurjchem-503	77	1	m.p	m.p	PROPN
eurjchem-503	77	2	.	.	PROPN
eurjchem-503	77	3	:	:	PUNCT
eurjchem-503	78	1	265‐266	265‐266	NUM
eurjchem-503	78	2	oc	oc	VERB
eurjchem-503	78	3	.	.	PROPN
eurjchem-503	78	4	ir	ir	PROPN
eurjchem-503	78	5	(	(	PUNCT
eurjchem-503	78	6	max	max	PROPN
eurjchem-503	78	7	,	,	PUNCT
eurjchem-503	78	8	thin	thin	ADJ
eurjchem-503	78	9	film	film	NOUN
eurjchem-503	78	10	,	,	PUNCT
eurjchem-503	78	11	cm‐	cm‐	NOUN
eurjchem-503	78	12	1	1	NUM
eurjchem-503	78	13	):	):	PUNCT
eurjchem-503	78	14	3317	3317	NUM
eurjchem-503	78	15	(	(	PUNCT
eurjchem-503	78	16	nh	nh	NOUN
eurjchem-503	78	17	)	)	PUNCT
eurjchem-503	78	18	,	,	PUNCT
eurjchem-503	78	19	1694	1694	NUM
eurjchem-503	78	20	and	and	CCONJ
eurjchem-503	78	21	1656	1656	NUM
eurjchem-503	78	22	(	(	PUNCT
eurjchem-503	78	23	c	c	NOUN
eurjchem-503	78	24	=	=	SYM
eurjchem-503	78	25	c	c	NOUN
eurjchem-503	78	26	)	)	PUNCT
eurjchem-503	78	27	,	,	PUNCT
eurjchem-503	78	28	1595	1595	NUM
eurjchem-503	78	29	(	(	PUNCT
eurjchem-503	78	30	nco	nco	NOUN
eurjchem-503	78	31	)	)	PUNCT
eurjchem-503	78	32	.	.	PUNCT
eurjchem-503	79	1	1h	1h	NUM
eurjchem-503	79	2	nmr	nmr	NOUN
eurjchem-503	79	3	(	(	PUNCT
eurjchem-503	79	4	400	400	NUM
eurjchem-503	79	5	mhz	mhz	NOUN
eurjchem-503	79	6	,	,	PUNCT
eurjchem-503	79	7	cdcl3	cdcl3	NOUN
eurjchem-503	79	8	,	,	PUNCT
eurjchem-503	79	9			NUM
eurjchem-503	79	10	,	,	PUNCT
eurjchem-503	79	11	ppm	ppm	NUM
eurjchem-503	79	12	):	):	PUNCT
eurjchem-503	79	13	10.7	10.7	NUM
eurjchem-503	79	14	(	(	PUNCT
eurjchem-503	79	15	1h	1h	NUM
eurjchem-503	79	16	,	,	PUNCT
eurjchem-503	79	17	s	s	X
eurjchem-503	79	18	,	,	PUNCT
eurjchem-503	79	19	nh	nh	PROPN
eurjchem-503	79	20	)	)	PUNCT
eurjchem-503	79	21	,	,	PUNCT
eurjchem-503	79	22	7.34	7.34	NUM
eurjchem-503	79	23	(	(	PUNCT
eurjchem-503	79	24	1h	1h	NUM
eurjchem-503	79	25	,	,	PUNCT
eurjchem-503	79	26	d	d	PROPN
eurjchem-503	79	27	,	,	PUNCT
eurjchem-503	79	28	j=8.5	j=8.5	PROPN
eurjchem-503	79	29	hz	hz	NOUN
eurjchem-503	79	30	,	,	PUNCT
eurjchem-503	79	31	9‐	9‐	NUM
eurjchem-503	79	32	h	h	NOUN
eurjchem-503	79	33	)	)	PUNCT
eurjchem-503	79	34	,	,	PUNCT
eurjchem-503	79	35	6.86	6.86	NUM
eurjchem-503	79	36	(	(	PUNCT
eurjchem-503	79	37	1h	1h	NUM
eurjchem-503	79	38	,	,	PUNCT
eurjchem-503	79	39	d	d	PROPN
eurjchem-503	79	40	,	,	PUNCT
eurjchem-503	79	41	2.0	2.0	NUM
eurjchem-503	79	42	hz	hz	NOUN
eurjchem-503	79	43	,	,	PUNCT
eurjchem-503	79	44	12‐h	12‐h	NUM
eurjchem-503	79	45	)	)	PUNCT
eurjchem-503	79	46	,	,	PUNCT
eurjchem-503	79	47	6.77	6.77	NUM
eurjchem-503	79	48	(	(	PUNCT
eurjchem-503	79	49	1h	1h	NUM
eurjchem-503	79	50	,	,	PUNCT
eurjchem-503	79	51	dd	dd	NOUN
eurjchem-503	79	52	,	,	PUNCT
eurjchem-503	79	53	j	j	PROPN
eurjchem-503	80	1	=	=	SYM
eurjchem-503	80	2	8.5	8.5	NUM
eurjchem-503	80	3	and	and	CCONJ
eurjchem-503	80	4	2.0	2.0	NUM
eurjchem-503	80	5	hz	hz	NOUN
eurjchem-503	80	6	,	,	PUNCT
eurjchem-503	80	7	10‐h	10‐h	NUM
eurjchem-503	80	8	)	)	PUNCT
eurjchem-503	80	9	,	,	PUNCT
eurjchem-503	80	10	6.63	6.63	NUM
eurjchem-503	80	11	(	(	PUNCT
eurjchem-503	80	12	1h	1h	NUM
eurjchem-503	80	13	,	,	PUNCT
eurjchem-503	80	14	m	m	PROPN
eurjchem-503	80	15	,	,	PUNCT
eurjchem-503	80	16	19‐h	19‐h	NUM
eurjchem-503	80	17	)	)	PUNCT
eurjchem-503	80	18	,	,	PUNCT
eurjchem-503	80	19	4.91	4.91	NUM
eurjchem-503	80	20	(	(	PUNCT
eurjchem-503	80	21	1h	1h	NUM
eurjchem-503	80	22	,	,	PUNCT
eurjchem-503	80	23	brdd	brdd	NOUN
eurjchem-503	80	24	,	,	PUNCT
eurjchem-503	80	25	j	j	NOUN
eurjchem-503	81	1	=	=	SYM
eurjchem-503	81	2	12	12	NUM
eurjchem-503	81	3	and	and	CCONJ
eurjchem-503	81	4	4	4	NUM
eurjchem-503	81	5	hz	hz	NOUN
eurjchem-503	81	6	,	,	PUNCT
eurjchem-503	81	7	3‐h	3‐h	NUM
eurjchem-503	81	8	)	)	PUNCT
eurjchem-503	81	9	,	,	PUNCT
eurjchem-503	81	10	4.66	4.66	NUM
eurjchem-503	81	11	(	(	PUNCT
eurjchem-503	81	12	1h	1h	NUM
eurjchem-503	81	13	,	,	PUNCT
eurjchem-503	81	14	s	s	PROPN
eurjchem-503	81	15	,	,	PUNCT
eurjchem-503	81	16	16‐h	16‐h	NUM
eurjchem-503	81	17	)	)	PUNCT
eurjchem-503	81	18	,	,	PUNCT
eurjchem-503	81	19	3.75	3.75	NUM
eurjchem-503	81	20	(	(	PUNCT
eurjchem-503	81	21	3h	3h	NUM
eurjchem-503	81	22	,	,	PUNCT
eurjchem-503	81	23	s	s	X
eurjchem-503	81	24	,	,	PUNCT
eurjchem-503	81	25	ome	ome	PROPN
eurjchem-503	81	26	*	*	NUM
eurjchem-503	81	27	)	)	PUNCT
eurjchem-503	81	28	(	(	PUNCT
eurjchem-503	82	1	*	*	PUNCT
eurjchem-503	82	2	methoxy	methoxy	NOUN
eurjchem-503	82	3	attached	attach	VERB
eurjchem-503	82	4	to	to	ADP
eurjchem-503	82	5	the	the	DET
eurjchem-503	82	6	aromatic	aromatic	ADJ
eurjchem-503	82	7	ring	ring	NOUN
eurjchem-503	82	8	a	a	NOUN
eurjchem-503	82	9	)	)	PUNCT
eurjchem-503	82	10	,	,	PUNCT
eurjchem-503	82	11	3.52	3.52	NUM
eurjchem-503	82	12	(	(	PUNCT
eurjchem-503	82	13	3h	3h	NUM
eurjchem-503	82	14	,	,	PUNCT
eurjchem-503	82	15	s	s	X
eurjchem-503	82	16	,	,	PUNCT
eurjchem-503	82	17	ome	ome	PROPN
eurjchem-503	82	18	)	)	PUNCT
eurjchem-503	82	19	,	,	PUNCT
eurjchem-503	82	20	2.59‐2.49	2.59‐2.49	NUM
eurjchem-503	82	21	(	(	PUNCT
eurjchem-503	82	22	6h	6h	NUM
eurjchem-503	82	23	,	,	PUNCT
eurjchem-503	82	24	m	m	PROPN
eurjchem-503	82	25	,	,	PUNCT
eurjchem-503	82	26	18‐h2	18‐h2	PROPN
eurjchem-503	82	27	,	,	PUNCT
eurjchem-503	82	28	6‐	6‐	NUM
eurjchem-503	82	29	h2	h2	NOUN
eurjchem-503	82	30	,	,	PUNCT
eurjchem-503	82	31	and	and	CCONJ
eurjchem-503	82	32	5‐h2	5‐h2	NUM
eurjchem-503	82	33	)	)	PUNCT
eurjchem-503	82	34	,	,	PUNCT
eurjchem-503	82	35	3.15	3.15	NUM
eurjchem-503	82	36	(	(	PUNCT
eurjchem-503	82	37	1h	1h	NUM
eurjchem-503	82	38	,	,	PUNCT
eurjchem-503	82	39	m	m	PROPN
eurjchem-503	82	40	,	,	PUNCT
eurjchem-503	82	41	15‐h	15‐h	NUM
eurjchem-503	82	42	)	)	PUNCT
eurjchem-503	82	43	,	,	PUNCT
eurjchem-503	82	44	2.37	2.37	NUM
eurjchem-503	82	45	(	(	PUNCT
eurjchem-503	82	46	1h	1h	NUM
eurjchem-503	82	47	,	,	PUNCT
eurjchem-503	82	48	ddd	ddd	PROPN
eurjchem-503	82	49	,	,	PUNCT
eurjchem-503	82	50	j	j	NOUN
eurjchem-503	82	51	=	=	PROPN
eurjchem-503	82	52	12.5	12.5	NUM
eurjchem-503	82	53	,	,	PUNCT
eurjchem-503	82	54	4	4	NUM
eurjchem-503	82	55	,	,	PUNCT
eurjchem-503	82	56	and	and	CCONJ
eurjchem-503	82	57	3.5	3.5	NUM
eurjchem-503	82	58	hz	hz	NOUN
eurjchem-503	82	59	,	,	PUNCT
eurjchem-503	82	60	14‐heq	14‐heq	NUM
eurjchem-503	82	61	)	)	PUNCT
eurjchem-503	82	62	,	,	PUNCT
eurjchem-503	82	63	1.22‐1.18	1.22‐1.18	NUM
eurjchem-503	82	64	(	(	PUNCT
eurjchem-503	82	65	1h	1h	NUM
eurjchem-503	82	66	,	,	PUNCT
eurjchem-503	82	67	m	m	PROPN
eurjchem-503	82	68	,	,	PUNCT
eurjchem-503	82	69	14‐hax	14‐hax	NUM
eurjchem-503	82	70	)	)	PUNCT
eurjchem-503	82	71	.	.	PUNCT
eurjchem-503	83	1	ms	ms	NOUN
eurjchem-503	83	2	(	(	PUNCT
eurjchem-503	83	3	m	m	PROPN
eurjchem-503	83	4	/	/	SYM
eurjchem-503	83	5	z	z	NOUN
eurjchem-503	83	6	,	,	PUNCT
eurjchem-503	83	7	ei	ei	PROPN
eurjchem-503	83	8	):	):	PUNCT
eurjchem-503	83	9	350	350	NUM
eurjchem-503	83	10	;	;	PUNCT
eurjchem-503	83	11	hrms	hrm	VERB
eurjchem-503	83	12	calcd	calcd	NOUN
eurjchem-503	83	13	.	.	PUNCT
eurjchem-503	84	1	for	for	ADP
eurjchem-503	84	2	c21h22n2o3	c21h22n2o3	PROPN
eurjchem-503	84	3	(	(	PUNCT
eurjchem-503	84	4	m+	m+	NUM
eurjchem-503	84	5	):	):	PUNCT
eurjchem-503	84	6	350.1630	350.1630	NUM
eurjchem-503	84	7	,	,	PUNCT
eurjchem-503	84	8	found	find	VERB
eurjchem-503	84	9	:	:	PUNCT
eurjchem-503	84	10	350.1627	350.1627	NUM
eurjchem-503	84	11	.	.	PUNCT
eurjchem-503	85	1	2.2.6	2.2.6	NUM
eurjchem-503	85	2	.	.	NOUN
eurjchem-503	85	3	11,17‐dimethoxy‐16,17,19,20‐	11,17‐dimethoxy‐16,17,19,20‐	NUM
eurjchem-503	85	4	tetrahydro‐yohimban	tetrahydro‐yohimban	INTJ
eurjchem-503	85	5	(	(	PUNCT
eurjchem-503	85	6	10	10	NUM
eurjchem-503	85	7	)	)	PUNCT
eurjchem-503	85	8	a	a	DET
eurjchem-503	85	9	solution	solution	NOUN
eurjchem-503	85	10	of	of	ADP
eurjchem-503	85	11	the	the	DET
eurjchem-503	85	12	lactam	lactam	NOUN
eurjchem-503	85	13	9	9	NUM
eurjchem-503	85	14	(	(	PUNCT
eurjchem-503	85	15	350	350	NUM
eurjchem-503	85	16	mg	mg	NOUN
eurjchem-503	85	17	,	,	PUNCT
eurjchem-503	85	18	1.00	1.00	NUM
eurjchem-503	85	19	mmol	mmol	NOUN
eurjchem-503	85	20	)	)	PUNCT
eurjchem-503	85	21	in	in	ADP
eurjchem-503	85	22	anhydrous	anhydrous	ADJ
eurjchem-503	85	23	thf	thf	NOUN
eurjchem-503	85	24	(	(	PUNCT
eurjchem-503	85	25	35	35	NUM
eurjchem-503	85	26	ml	ml	NOUN
eurjchem-503	85	27	)	)	PUNCT
eurjchem-503	85	28	was	be	AUX
eurjchem-503	85	29	added	add	VERB
eurjchem-503	85	30	dropwise	dropwise	NOUN
eurjchem-503	85	31	to	to	ADP
eurjchem-503	85	32	an	an	DET
eurjchem-503	85	33	ice‐cooled	ice‐coole	VERB
eurjchem-503	85	34	,	,	PUNCT
eurjchem-503	85	35	stirred	stir	VERB
eurjchem-503	85	36	solution	solution	NOUN
eurjchem-503	85	37	of	of	ADP
eurjchem-503	85	38	lithium	lithium	NOUN
eurjchem-503	85	39	aluminium	aluminium	NOUN
eurjchem-503	85	40	hydride	hydride	NOUN
eurjchem-503	85	41	(	(	PUNCT
eurjchem-503	85	42	525	525	NUM
eurjchem-503	85	43	mg	mg	PROPN
eurjchem-503	85	44	,	,	PUNCT
eurjchem-503	85	45	13.8	13.8	NUM
eurjchem-503	85	46	mmol	mmol	NOUN
eurjchem-503	85	47	)	)	PUNCT
eurjchem-503	85	48	in	in	ADP
eurjchem-503	85	49	anhydrous	anhydrous	ADJ
eurjchem-503	85	50	ether	ether	NOUN
eurjchem-503	85	51	(	(	PUNCT
eurjchem-503	85	52	35	35	NUM
eurjchem-503	85	53	ml	ml	NOUN
eurjchem-503	85	54	)	)	PUNCT
eurjchem-503	85	55	under	under	ADP
eurjchem-503	85	56	argon	argon	NOUN
eurjchem-503	85	57	.	.	PUNCT
eurjchem-503	86	1	after	after	ADP
eurjchem-503	86	2	being	be	AUX
eurjchem-503	86	3	refluxed	refluxe	VERB
eurjchem-503	86	4	for	for	ADP
eurjchem-503	86	5	2	2	NUM
eurjchem-503	86	6	h	h	NOUN
eurjchem-503	86	7	,	,	PUNCT
eurjchem-503	86	8	the	the	DET
eurjchem-503	86	9	reaction	reaction	NOUN
eurjchem-503	86	10	mixture	mixture	NOUN
eurjchem-503	86	11	was	be	AUX
eurjchem-503	86	12	allowed	allow	VERB
eurjchem-503	86	13	to	to	PART
eurjchem-503	86	14	cool	cool	VERB
eurjchem-503	86	15	and	and	CCONJ
eurjchem-503	86	16	sufficient	sufficient	ADJ
eurjchem-503	86	17	amount	amount	NOUN
eurjchem-503	86	18	of	of	ADP
eurjchem-503	86	19	ethyl	ethyl	PROPN
eurjchem-503	86	20	acetate	acetate	PROPN
eurjchem-503	86	21	was	be	AUX
eurjchem-503	86	22	added	add	VERB
eurjchem-503	86	23	dropwise	dropwise	NOUN
eurjchem-503	86	24	by	by	ADP
eurjchem-503	86	25	keeping	keep	VERB
eurjchem-503	86	26	the	the	DET
eurjchem-503	86	27	reaction	reaction	NOUN
eurjchem-503	86	28	mixture	mixture	NOUN
eurjchem-503	86	29	in	in	ADP
eurjchem-503	86	30	the	the	DET
eurjchem-503	86	31	ice‐cooled	ice‐coole	VERB
eurjchem-503	86	32	water	water	NOUN
eurjchem-503	86	33	in	in	ADP
eurjchem-503	86	34	order	order	NOUN
eurjchem-503	86	35	to	to	PART
eurjchem-503	86	36	decompose	decompose	VERB
eurjchem-503	86	37	the	the	DET
eurjchem-503	86	38	lah	lah	NOUN
eurjchem-503	86	39	completely	completely	ADV
eurjchem-503	86	40	.	.	PUNCT
eurjchem-503	87	1	after	after	ADP
eurjchem-503	87	2	filtration	filtration	NOUN
eurjchem-503	87	3	the	the	DET
eurjchem-503	87	4	reaction	reaction	NOUN
eurjchem-503	87	5	mixture	mixture	NOUN
eurjchem-503	87	6	was	be	AUX
eurjchem-503	87	7	extracted	extract	VERB
eurjchem-503	87	8	with	with	ADP
eurjchem-503	87	9	ethyl	ethyl	PROPN
eurjchem-503	87	10	acetate	acetate	NOUN
eurjchem-503	87	11	.	.	PUNCT
eurjchem-503	88	1	the	the	DET
eurjchem-503	88	2	extract	extract	NOUN
eurjchem-503	88	3	was	be	AUX
eurjchem-503	88	4	dried	dry	VERB
eurjchem-503	88	5	and	and	CCONJ
eurjchem-503	88	6	evaporated	evaporate	VERB
eurjchem-503	88	7	to	to	PART
eurjchem-503	88	8	give	give	VERB
eurjchem-503	88	9	the	the	DET
eurjchem-503	88	10	amine	amine	ADJ
eurjchem-503	88	11	10	10	NUM
eurjchem-503	88	12	as	as	ADP
eurjchem-503	88	13	pale	pale	ADJ
eurjchem-503	88	14	yellow	yellow	ADJ
eurjchem-503	88	15	crystals	crystal	NOUN
eurjchem-503	88	16	(	(	PUNCT
eurjchem-503	88	17	scheme	scheme	NOUN
eurjchem-503	88	18	3	3	NUM
eurjchem-503	88	19	)	)	PUNCT
eurjchem-503	88	20	.	.	PUNCT
eurjchem-503	89	1	m.p	m.p	PROPN
eurjchem-503	89	2	.	.	PROPN
eurjchem-503	89	3	:	:	PUNCT
eurjchem-503	90	1	198‐200	198‐200	NUM
eurjchem-503	90	2	oc	oc	PROPN
eurjchem-503	90	3	.	.	PROPN
eurjchem-503	90	4	yield	yield	NOUN
eurjchem-503	90	5	:	:	PUNCT
eurjchem-503	90	6	324	324	NUM
eurjchem-503	90	7	mg	mg	NOUN
eurjchem-503	90	8	,	,	PUNCT
eurjchem-503	90	9	96	96	NUM
eurjchem-503	90	10	%	%	NOUN
eurjchem-503	90	11	.	.	PUNCT
eurjchem-503	91	1	ir	ir	INTJ
eurjchem-503	91	2	(	(	PUNCT
eurjchem-503	91	3	max	max	PROPN
eurjchem-503	91	4	,	,	PUNCT
eurjchem-503	91	5	thin	thin	ADJ
eurjchem-503	91	6	film	film	NOUN
eurjchem-503	91	7	,	,	PUNCT
eurjchem-503	91	8	cm‐1	cm‐1	PROPN
eurjchem-503	91	9	):	):	PUNCT
eurjchem-503	91	10	3359	3359	NUM
eurjchem-503	91	11	(	(	PUNCT
eurjchem-503	91	12	nh	nh	NOUN
eurjchem-503	91	13	)	)	PUNCT
eurjchem-503	91	14	,	,	PUNCT
eurjchem-503	91	15	1699	1699	NUM
eurjchem-503	91	16	and	and	CCONJ
eurjchem-503	91	17	1651	1651	NUM
eurjchem-503	91	18	(	(	PUNCT
eurjchem-503	91	19	c	c	NOUN
eurjchem-503	91	20	=	=	SYM
eurjchem-503	91	21	c	c	NOUN
eurjchem-503	91	22	)	)	PUNCT
eurjchem-503	91	23	.	.	PUNCT
eurjchem-503	92	1	1h	1h	NUM
eurjchem-503	92	2	nmr	nmr	NOUN
eurjchem-503	92	3	(	(	PUNCT
eurjchem-503	92	4	400	400	NUM
eurjchem-503	92	5	mhz	mhz	NOUN
eurjchem-503	92	6	,	,	PUNCT
eurjchem-503	92	7	cdcl3	cdcl3	NOUN
eurjchem-503	92	8	,	,	PUNCT
eurjchem-503	92	9			NUM
eurjchem-503	92	10	,	,	PUNCT
eurjchem-503	92	11	ppm	ppm	NUM
eurjchem-503	92	12	):	):	PUNCT
eurjchem-503	92	13	10.2	10.2	NUM
eurjchem-503	92	14	(	(	PUNCT
eurjchem-503	92	15	1h	1h	NUM
eurjchem-503	92	16	,	,	PUNCT
eurjchem-503	92	17	s	s	X
eurjchem-503	92	18	,	,	PUNCT
eurjchem-503	92	19	nh	nh	PROPN
eurjchem-503	92	20	)	)	PUNCT
eurjchem-503	92	21	,	,	PUNCT
eurjchem-503	92	22	7.32	7.32	NUM
eurjchem-503	92	23	(	(	PUNCT
eurjchem-503	92	24	1h	1h	NUM
eurjchem-503	92	25	,	,	PUNCT
eurjchem-503	92	26	d	d	PROPN
eurjchem-503	92	27	,	,	PUNCT
eurjchem-503	92	28	j	j	PROPN
eurjchem-503	92	29	=	=	SYM
eurjchem-503	92	30	8.5	8.5	NUM
eurjchem-503	92	31	hz	hz	VERB
eurjchem-503	92	32	,	,	PUNCT
eurjchem-503	92	33	9‐	9‐	NUM
eurjchem-503	92	34	h	h	NOUN
eurjchem-503	92	35	)	)	PUNCT
eurjchem-503	92	36	,	,	PUNCT
eurjchem-503	92	37	6.83	6.83	NUM
eurjchem-503	92	38	(	(	PUNCT
eurjchem-503	92	39	1h	1h	NUM
eurjchem-503	92	40	,	,	PUNCT
eurjchem-503	92	41	d	d	PROPN
eurjchem-503	92	42	,	,	PUNCT
eurjchem-503	92	43	2.0	2.0	NUM
eurjchem-503	92	44	hz	hz	NOUN
eurjchem-503	92	45	,	,	PUNCT
eurjchem-503	92	46	12‐h	12‐h	NUM
eurjchem-503	92	47	)	)	PUNCT
eurjchem-503	92	48	,	,	PUNCT
eurjchem-503	92	49	6.71	6.71	NUM
eurjchem-503	92	50	(	(	PUNCT
eurjchem-503	92	51	1h	1h	NUM
eurjchem-503	92	52	,	,	PUNCT
eurjchem-503	92	53	dd	dd	NOUN
eurjchem-503	92	54	,	,	PUNCT
eurjchem-503	92	55	j	j	PROPN
eurjchem-503	93	1	=	=	SYM
eurjchem-503	93	2	8.5	8.5	NUM
eurjchem-503	93	3	,	,	PUNCT
eurjchem-503	93	4	2.0	2.0	NUM
eurjchem-503	93	5	hz	hz	NOUN
eurjchem-503	93	6	,	,	PUNCT
eurjchem-503	93	7	10‐h	10‐h	NUM
eurjchem-503	93	8	)	)	PUNCT
eurjchem-503	93	9	,	,	PUNCT
eurjchem-503	93	10	5.42	5.42	NUM
eurjchem-503	93	11	(	(	PUNCT
eurjchem-503	93	12	1h	1h	NUM
eurjchem-503	93	13	,	,	PUNCT
eurjchem-503	93	14	br	br	PROPN
eurjchem-503	93	15	s	s	PROPN
eurjchem-503	93	16	,	,	PUNCT
eurjchem-503	93	17	19‐h	19‐h	NUM
eurjchem-503	93	18	)	)	PUNCT
eurjchem-503	93	19	,	,	PUNCT
eurjchem-503	93	20	4.48	4.48	NUM
eurjchem-503	93	21	(	(	PUNCT
eurjchem-503	93	22	1h	1h	NUM
eurjchem-503	93	23	,	,	PUNCT
eurjchem-503	93	24	brs	br	VERB
eurjchem-503	93	25	,	,	PUNCT
eurjchem-503	93	26	16‐h	16‐h	NUM
eurjchem-503	93	27	)	)	PUNCT
eurjchem-503	93	28	,	,	PUNCT
eurjchem-503	93	29	3.77	3.77	NUM
eurjchem-503	93	30	(	(	PUNCT
eurjchem-503	93	31	3h	3h	NUM
eurjchem-503	93	32	,	,	PUNCT
eurjchem-503	93	33	s	s	X
eurjchem-503	93	34	,	,	PUNCT
eurjchem-503	93	35	ome	ome	PROPN
eurjchem-503	93	36	)	)	PUNCT
eurjchem-503	93	37	,	,	PUNCT
eurjchem-503	93	38	3.58	3.58	NUM
eurjchem-503	93	39	(	(	PUNCT
eurjchem-503	93	40	3h	3h	NUM
eurjchem-503	93	41	,	,	PUNCT
eurjchem-503	93	42	s	s	X
eurjchem-503	93	43	,	,	PUNCT
eurjchem-503	93	44	ome	ome	PROPN
eurjchem-503	93	45	)	)	PUNCT
eurjchem-503	93	46	,	,	PUNCT
eurjchem-503	93	47	3.60	3.60	NUM
eurjchem-503	93	48	(	(	PUNCT
eurjchem-503	93	49	1h	1h	NUM
eurjchem-503	93	50	,	,	PUNCT
eurjchem-503	93	51	br	br	PROPN
eurjchem-503	93	52	,	,	PUNCT
eurjchem-503	93	53	dd	dd	NOUN
eurjchem-503	93	54	,	,	PUNCT
eurjchem-503	93	55	j	j	PROPN
eurjchem-503	94	1	=	=	SYM
eurjchem-503	94	2	12	12	NUM
eurjchem-503	94	3	and	and	CCONJ
eurjchem-503	94	4	2.5	2.5	NUM
eurjchem-503	94	5	hz	hz	NOUN
eurjchem-503	94	6	,	,	PUNCT
eurjchem-503	94	7	3‐h	3‐h	NUM
eurjchem-503	94	8	)	)	PUNCT
eurjchem-503	94	9	,	,	PUNCT
eurjchem-503	94	10	3.40	3.40	NUM
eurjchem-503	94	11	and	and	CCONJ
eurjchem-503	94	12	3.0	3.0	NUM
eurjchem-503	94	13	(	(	PUNCT
eurjchem-503	94	14	2h	2h	NUM
eurjchem-503	94	15	,	,	PUNCT
eurjchem-503	94	16	abq	abq	PROPN
eurjchem-503	94	17	,	,	PUNCT
eurjchem-503	94	18	j	j	PROPN
eurjchem-503	95	1	=	=	PROPN
eurjchem-503	95	2	12	12	NUM
eurjchem-503	95	3	hz	hz	VERB
eurjchem-503	95	4	,	,	PUNCT
eurjchem-503	95	5	21‐h2	21‐h2	PROPN
eurjchem-503	95	6	)	)	PUNCT
eurjchem-503	95	7	,	,	PUNCT
eurjchem-503	95	8	3.59	3.59	NUM
eurjchem-503	95	9	(	(	PUNCT
eurjchem-503	95	10	1h	1h	NUM
eurjchem-503	95	11	,	,	PUNCT
eurjchem-503	95	12	m	m	PROPN
eurjchem-503	95	13	,	,	PUNCT
eurjchem-503	95	14	15‐h	15‐h	NUM
eurjchem-503	95	15	)	)	PUNCT
eurjchem-503	95	16	,	,	PUNCT
eurjchem-503	95	17	2.79‐	2.79‐	NUM
eurjchem-503	95	18	2.67	2.67	NUM
eurjchem-503	95	19	(	(	PUNCT
eurjchem-503	95	20	6h	6h	NUM
eurjchem-503	95	21	,	,	PUNCT
eurjchem-503	95	22	m	m	PROPN
eurjchem-503	95	23	,	,	PUNCT
eurjchem-503	95	24	18‐h2	18‐h2	PROPN
eurjchem-503	95	25	,	,	PUNCT
eurjchem-503	95	26	6‐h2	6‐h2	NUM
eurjchem-503	95	27	,	,	PUNCT
eurjchem-503	95	28	and	and	CCONJ
eurjchem-503	95	29	5‐h2	5‐h2	NUM
eurjchem-503	95	30	)	)	PUNCT
eurjchem-503	95	31	,	,	PUNCT
eurjchem-503	95	32	2.50	2.50	NUM
eurjchem-503	95	33	(	(	PUNCT
eurjchem-503	95	34	1	1	NUM
eurjchem-503	95	35	h	h	NOUN
eurjchem-503	95	36	,	,	PUNCT
eurjchem-503	95	37	ddd	ddd	PROPN
eurjchem-503	95	38	,	,	PUNCT
eurjchem-503	95	39	j	j	NOUN
eurjchem-503	96	1	=	=	SYM
eurjchem-503	96	2	12	12	NUM
eurjchem-503	96	3	,	,	PUNCT
eurjchem-503	96	4	4.5	4.5	NUM
eurjchem-503	96	5	and	and	CCONJ
eurjchem-503	96	6	2.5	2.5	NUM
eurjchem-503	96	7	hz	hz	NOUN
eurjchem-503	96	8	,	,	PUNCT
eurjchem-503	96	9	14‐heq	14‐heq	NUM
eurjchem-503	96	10	)	)	PUNCT
eurjchem-503	96	11	,	,	PUNCT
eurjchem-503	96	12	and	and	CCONJ
eurjchem-503	96	13	1.40	1.40	NUM
eurjchem-503	96	14	(	(	PUNCT
eurjchem-503	96	15	1h	1h	NUM
eurjchem-503	96	16	,	,	PUNCT
eurjchem-503	96	17	q	q	NOUN
eurjchem-503	96	18	,	,	PUNCT
eurjchem-503	96	19	j	j	PROPN
eurjchem-503	97	1	=	=	PROPN
eurjchem-503	97	2	12	12	NUM
eurjchem-503	97	3	hz	hz	VERB
eurjchem-503	97	4	,	,	PUNCT
eurjchem-503	97	5	14‐hax	14‐hax	NUM
eurjchem-503	97	6	)	)	PUNCT
eurjchem-503	97	7	.	.	PUNCT
eurjchem-503	98	1	ms	ms	NOUN
eurjchem-503	98	2	(	(	PUNCT
eurjchem-503	98	3	m	m	PROPN
eurjchem-503	98	4	/	/	SYM
eurjchem-503	98	5	z	z	NOUN
eurjchem-503	98	6	,	,	PUNCT
eurjchem-503	98	7	ei	ei	NOUN
eurjchem-503	98	8	):	):	PUNCT
eurjchem-503	98	9	336	336	NUM
eurjchem-503	98	10	;	;	PUNCT
eurjchem-503	98	11	hrms	hrm	VERB
eurjchem-503	98	12	calcd	calcd	NOUN
eurjchem-503	98	13	.	.	PUNCT
eurjchem-503	99	1	for	for	ADP
eurjchem-503	99	2	c21h24n2o2	c21h24n2o2	NOUN
eurjchem-503	99	3	(	(	PUNCT
eurjchem-503	99	4	m+	m+	NUM
eurjchem-503	99	5	):	):	PUNCT
eurjchem-503	99	6	336.1838	336.1838	NUM
eurjchem-503	99	7	,	,	PUNCT
eurjchem-503	99	8	found	find	VERB
eurjchem-503	99	9	:	:	PUNCT
eurjchem-503	100	1	336.1837	336.1837	NUM
eurjchem-503	100	2	.	.	PUNCT
eurjchem-503	101	1	2.2.7	2.2.7	X
eurjchem-503	101	2	.	.	PUNCT
eurjchem-503	102	1	11‐methoxy‐19,20‐didehydroyohimban‐17‐one	11‐methoxy‐19,20‐didehydroyohimban‐17‐one	NUM
eurjchem-503	102	2	(	(	PUNCT
eurjchem-503	102	3	11	11	NUM
eurjchem-503	102	4	)	)	SYM
eurjchem-503	102	5	10	10	NUM
eurjchem-503	102	6	%	%	NOUN
eurjchem-503	102	7	hydrochloric	hydrochloric	ADJ
eurjchem-503	102	8	acid	acid	NOUN
eurjchem-503	102	9	(	(	PUNCT
eurjchem-503	102	10	18	18	NUM
eurjchem-503	102	11	ml	ml	NOUN
eurjchem-503	102	12	)	)	PUNCT
eurjchem-503	102	13	was	be	AUX
eurjchem-503	102	14	added	add	VERB
eurjchem-503	102	15	to	to	ADP
eurjchem-503	102	16	a	a	DET
eurjchem-503	102	17	solution	solution	NOUN
eurjchem-503	102	18	of	of	ADP
eurjchem-503	102	19	the	the	DET
eurjchem-503	102	20	amine	amine	ADJ
eurjchem-503	102	21	10	10	NUM
eurjchem-503	102	22	(	(	PUNCT
eurjchem-503	102	23	250	250	NUM
eurjchem-503	102	24	mg	mg	NOUN
eurjchem-503	102	25	,	,	PUNCT
eurjchem-503	102	26	0.744	0.744	NUM
eurjchem-503	102	27	mmol	mmol	NOUN
eurjchem-503	102	28	)	)	PUNCT
eurjchem-503	102	29	in	in	ADP
eurjchem-503	102	30	methanol	methanol	NOUN
eurjchem-503	102	31	(	(	PUNCT
eurjchem-503	102	32	15	15	NUM
eurjchem-503	102	33	ml	ml	NOUN
eurjchem-503	102	34	)	)	PUNCT
eurjchem-503	102	35	.	.	PUNCT
eurjchem-503	103	1	after	after	ADP
eurjchem-503	103	2	being	be	AUX
eurjchem-503	103	3	stirred	stir	VERB
eurjchem-503	103	4	at	at	ADP
eurjchem-503	103	5	room	room	NOUN
eurjchem-503	103	6	temperature	temperature	NOUN
eurjchem-503	103	7	under	under	ADP
eurjchem-503	103	8	argon	argon	NOUN
eurjchem-503	103	9	atmosphere	atmosphere	NOUN
eurjchem-503	103	10	for	for	ADP
eurjchem-503	103	11	1	1	NUM
eurjchem-503	103	12	h	h	NOUN
eurjchem-503	103	13	,	,	PUNCT
eurjchem-503	103	14	the	the	DET
eurjchem-503	103	15	reaction	reaction	NOUN
eurjchem-503	103	16	mixture	mixture	NOUN
eurjchem-503	103	17	was	be	AUX
eurjchem-503	103	18	evaporated	evaporate	VERB
eurjchem-503	103	19	.	.	PUNCT
eurjchem-503	104	1	water	water	NOUN
eurjchem-503	104	2	(	(	PUNCT
eurjchem-503	104	3	5	5	NUM
eurjchem-503	104	4	ml	ml	NOUN
eurjchem-503	104	5	)	)	PUNCT
eurjchem-503	104	6	was	be	AUX
eurjchem-503	104	7	added	add	VERB
eurjchem-503	104	8	to	to	ADP
eurjchem-503	104	9	the	the	DET
eurjchem-503	104	10	residue	residue	NOUN
eurjchem-503	104	11	and	and	CCONJ
eurjchem-503	104	12	the	the	DET
eurjchem-503	104	13	mixture	mixture	NOUN
eurjchem-503	104	14	was	be	AUX
eurjchem-503	104	15	made	make	VERB
eurjchem-503	104	16	alkaline	alkaline	NOUN
eurjchem-503	104	17	by	by	ADP
eurjchem-503	104	18	the	the	DET
eurjchem-503	104	19	addition	addition	NOUN
eurjchem-503	104	20	of	of	ADP
eurjchem-503	104	21	saturated	saturated	ADJ
eurjchem-503	104	22	aqueous	aqueous	ADJ
eurjchem-503	104	23	sodium	sodium	NOUN
eurjchem-503	104	24	hydrogen	hydrogen	NOUN
eurjchem-503	104	25	carbonate	carbonate	NOUN
eurjchem-503	104	26	,	,	PUNCT
eurjchem-503	104	27	and	and	CCONJ
eurjchem-503	104	28	then	then	ADV
eurjchem-503	104	29	extracted	extract	VERB
eurjchem-503	104	30	with	with	ADP
eurjchem-503	104	31	dichloromethane	dichloromethane	NOUN
eurjchem-503	104	32	.	.	PUNCT
eurjchem-503	105	1	the	the	DET
eurjchem-503	105	2	organic	organic	ADJ
eurjchem-503	105	3	layer	layer	NOUN
eurjchem-503	105	4	was	be	AUX
eurjchem-503	105	5	washed	wash	VERB
eurjchem-503	105	6	,	,	PUNCT
eurjchem-503	105	7	dried	dry	VERB
eurjchem-503	105	8	,	,	PUNCT
eurjchem-503	105	9	and	and	CCONJ
eurjchem-503	105	10	evaporated	evaporate	VERB
eurjchem-503	105	11	to	to	PART
eurjchem-503	105	12	give	give	VERB
eurjchem-503	105	13	a	a	DET
eurjchem-503	105	14	dark	dark	ADJ
eurjchem-503	105	15	brownish	brownish	ADJ
eurjchem-503	105	16	solid	solid	NOUN
eurjchem-503	105	17	,	,	PUNCT
eurjchem-503	105	18	which	which	PRON
eurjchem-503	105	19	was	be	AUX
eurjchem-503	105	20	triturated	triturate	VERB
eurjchem-503	105	21	with	with	ADP
eurjchem-503	105	22	ether	ether	NOUN
eurjchem-503	105	23	to	to	PART
eurjchem-503	105	24	obtain	obtain	VERB
eurjchem-503	105	25	the	the	DET
eurjchem-503	105	26	nonconjugated	nonconjugated	ADJ
eurjchem-503	105	27	enone	enone	NOUN
eurjchem-503	105	28	,	,	PUNCT
eurjchem-503	105	29	11	11	NUM
eurjchem-503	105	30	,	,	PUNCT
eurjchem-503	105	31	as	as	SCONJ
eurjchem-503	105	32	light	light	ADJ
eurjchem-503	105	33	brown	brown	ADJ
eurjchem-503	105	34	solid	solid	ADJ
eurjchem-503	105	35	which	which	PRON
eurjchem-503	105	36	was	be	AUX
eurjchem-503	105	37	further	far	ADV
eurjchem-503	105	38	purified	purify	VERB
eurjchem-503	105	39	by	by	ADP
eurjchem-503	105	40	recrystallization	recrystallization	NOUN
eurjchem-503	105	41	from	from	ADP
eurjchem-503	105	42	methanol	methanol	NOUN
eurjchem-503	105	43	to	to	PART
eurjchem-503	105	44	afford	afford	VERB
eurjchem-503	105	45	colorless	colorless	ADJ
eurjchem-503	105	46	crystals	crystal	NOUN
eurjchem-503	105	47	(	(	PUNCT
eurjchem-503	105	48	scheme	scheme	NOUN
eurjchem-503	105	49	3	3	NUM
eurjchem-503	105	50	)	)	PUNCT
eurjchem-503	105	51	.	.	PUNCT
eurjchem-503	106	1	m.p	m.p	PROPN
eurjchem-503	106	2	.	.	PROPN
eurjchem-503	106	3	:	:	PUNCT
eurjchem-503	107	1	178‐181	178‐181	NUM
eurjchem-503	107	2	oc	oc	PROPN
eurjchem-503	107	3	.	.	PROPN
eurjchem-503	107	4	yield	yield	NOUN
eurjchem-503	107	5	:	:	PUNCT
eurjchem-503	107	6	235	235	NUM
eurjchem-503	107	7	mg	mg	NOUN
eurjchem-503	107	8	,	,	PUNCT
eurjchem-503	107	9	98	98	NUM
eurjchem-503	107	10	%	%	NOUN
eurjchem-503	107	11	.	.	PUNCT
eurjchem-503	108	1	ir	ir	PROPN
eurjchem-503	108	2	(	(	PUNCT
eurjchem-503	108	3	max	max	PROPN
eurjchem-503	108	4	,	,	PUNCT
eurjchem-503	108	5	thin	thin	ADJ
eurjchem-503	108	6	film	film	NOUN
eurjchem-503	108	7	,	,	PUNCT
eurjchem-503	108	8	cm‐1	cm‐1	PROPN
eurjchem-503	108	9	):	):	PUNCT
eurjchem-503	108	10	3369	3369	NUM
eurjchem-503	108	11	(	(	PUNCT
eurjchem-503	108	12	nh	nh	NOUN
eurjchem-503	108	13	)	)	PUNCT
eurjchem-503	108	14	.	.	PUNCT
eurjchem-503	109	1	1h	1h	NUM
eurjchem-503	109	2	nmr	nmr	NOUN
eurjchem-503	109	3	(	(	PUNCT
eurjchem-503	109	4	400	400	NUM
eurjchem-503	109	5	mhz	mhz	NOUN
eurjchem-503	109	6	,	,	PUNCT
eurjchem-503	109	7	cdcl3	cdcl3	NOUN
eurjchem-503	109	8	,	,	PUNCT
eurjchem-503	109	9			NUM
eurjchem-503	109	10	,	,	PUNCT
eurjchem-503	109	11	ppm	ppm	NUM
eurjchem-503	109	12	):	):	PUNCT
eurjchem-503	109	13	10.5	10.5	NUM
eurjchem-503	109	14	(	(	PUNCT
eurjchem-503	109	15	1h	1h	NUM
eurjchem-503	109	16	,	,	PUNCT
eurjchem-503	109	17	s	s	X
eurjchem-503	109	18	,	,	PUNCT
eurjchem-503	109	19	nh	nh	PROPN
eurjchem-503	109	20	)	)	PUNCT
eurjchem-503	109	21	,	,	PUNCT
eurjchem-503	109	22	7.40	7.40	NUM
eurjchem-503	109	23	(	(	PUNCT
eurjchem-503	109	24	1h	1h	NUM
eurjchem-503	109	25	,	,	PUNCT
eurjchem-503	109	26	d	d	PROPN
eurjchem-503	109	27	,	,	PUNCT
eurjchem-503	109	28	j	j	PROPN
eurjchem-503	109	29	=	=	SYM
eurjchem-503	109	30	8.5	8.5	NUM
eurjchem-503	109	31	hz	hz	NOUN
eurjchem-503	109	32	,	,	PUNCT
eurjchem-503	109	33	9‐h	9‐h	NOUN
eurjchem-503	109	34	)	)	PUNCT
eurjchem-503	109	35	,	,	PUNCT
eurjchem-503	109	36	6.91	6.91	NUM
eurjchem-503	109	37	(	(	PUNCT
eurjchem-503	109	38	1h	1h	NUM
eurjchem-503	109	39	,	,	PUNCT
eurjchem-503	109	40	d	d	PROPN
eurjchem-503	109	41	,	,	PUNCT
eurjchem-503	109	42	j	j	PROPN
eurjchem-503	110	1	=	=	SYM
eurjchem-503	110	2	2.0	2.0	NUM
eurjchem-503	110	3	hz	hz	NOUN
eurjchem-503	110	4	,	,	PUNCT
eurjchem-503	110	5	12‐h	12‐h	NUM
eurjchem-503	110	6	)	)	PUNCT
eurjchem-503	110	7	,	,	PUNCT
eurjchem-503	110	8	6.82	6.82	NUM
eurjchem-503	110	9	(	(	PUNCT
eurjchem-503	110	10	1h	1h	NUM
eurjchem-503	110	11	,	,	PUNCT
eurjchem-503	110	12	dd	dd	NOUN
eurjchem-503	110	13	,	,	PUNCT
eurjchem-503	110	14	j	j	PROPN
eurjchem-503	111	1	=	=	SYM
eurjchem-503	111	2	8.5	8.5	NUM
eurjchem-503	111	3	,	,	PUNCT
eurjchem-503	111	4	2.0	2.0	NUM
eurjchem-503	111	5	hz	hz	NOUN
eurjchem-503	111	6	,	,	PUNCT
eurjchem-503	111	7	10‐h	10‐h	NUM
eurjchem-503	111	8	)	)	PUNCT
eurjchem-503	111	9	,	,	PUNCT
eurjchem-503	111	10	5.71	5.71	NUM
eurjchem-503	111	11	(	(	PUNCT
eurjchem-503	111	12	1h	1h	NUM
eurjchem-503	111	13	,	,	PUNCT
eurjchem-503	111	14	s‐like	s‐like	ADP
eurjchem-503	111	15	,	,	PUNCT
eurjchem-503	111	16	19‐	19‐	NUM
eurjchem-503	111	17	h	h	NOUN
eurjchem-503	111	18	)	)	PUNCT
eurjchem-503	111	19	,	,	PUNCT
eurjchem-503	111	20	3.80	3.80	NUM
eurjchem-503	111	21	(	(	PUNCT
eurjchem-503	111	22	3h	3h	NUM
eurjchem-503	111	23	,	,	PUNCT
eurjchem-503	111	24	s	s	X
eurjchem-503	111	25	,	,	PUNCT
eurjchem-503	111	26	ome	ome	PROPN
eurjchem-503	111	27	)	)	PUNCT
eurjchem-503	111	28	,	,	PUNCT
eurjchem-503	111	29	3.46	3.46	NUM
eurjchem-503	111	30	and	and	CCONJ
eurjchem-503	111	31	3.42	3.42	NUM
eurjchem-503	111	32	(	(	PUNCT
eurjchem-503	111	33	2h	2h	NUM
eurjchem-503	111	34	,	,	PUNCT
eurjchem-503	111	35	abq	abq	PROPN
eurjchem-503	111	36	,	,	PUNCT
eurjchem-503	111	37	j	j	PROPN
eurjchem-503	112	1	=	=	PROPN
eurjchem-503	112	2	12	12	NUM
eurjchem-503	112	3	hz	hz	VERB
eurjchem-503	112	4	,	,	PUNCT
eurjchem-503	112	5	21‐h2	21‐h2	PROPN
eurjchem-503	112	6	)	)	PUNCT
eurjchem-503	112	7	,	,	PUNCT
eurjchem-503	112	8	yar	yar	PROPN
eurjchem-503	112	9	et	et	PROPN
eurjchem-503	112	10	al	al	PROPN
eurjchem-503	112	11	.	.	PUNCT
eurjchem-503	112	12	/	/	SYM
eurjchem-503	112	13	european	european	PROPN
eurjchem-503	112	14	journal	journal	PROPN
eurjchem-503	112	15	of	of	ADP
eurjchem-503	112	16	chemistry	chemistry	NOUN
eurjchem-503	112	17	3	3	NUM
eurjchem-503	112	18	(	(	PUNCT
eurjchem-503	112	19	1	1	NUM
eurjchem-503	112	20	)	)	PUNCT
eurjchem-503	112	21	(	(	PUNCT
eurjchem-503	112	22	2012	2012	NUM
eurjchem-503	112	23	)	)	PUNCT
eurjchem-503	113	1	26‐31	26‐31	ADV
eurjchem-503	113	2	29	29	NUM
eurjchem-503	113	3	n	n	NOUN
eurjchem-503	113	4	h	h	NOUN
eurjchem-503	113	5	n	n	CCONJ
eurjchem-503	113	6	meo	meo	PROPN
eurjchem-503	113	7	h	h	NOUN
eurjchem-503	113	8	h	h	NOUN
eurjchem-503	113	9	h	h	NOUN
eurjchem-503	114	1	o	o	INTJ
eurjchem-503	114	2	ome	ome	INTJ
eurjchem-503	115	1	n	n	PRON
eurjchem-503	115	2	h	h	NOUN
eurjchem-503	115	3	n	n	CCONJ
eurjchem-503	115	4	meo	meo	PROPN
eurjchem-503	115	5	h	h	NOUN
eurjchem-503	115	6	h	h	NOUN
eurjchem-503	116	1	h	h	NOUN
eurjchem-503	117	1	o	o	NOUN
eurjchem-503	117	2	o	o	NOUN
eurjchem-503	117	3	n	n	CCONJ
eurjchem-503	117	4	h	h	NOUN
eurjchem-503	117	5	n	n	CCONJ
eurjchem-503	118	1	meo	meo	PROPN
eurjchem-503	118	2	h	h	NOUN
eurjchem-503	118	3	h	h	NOUN
eurjchem-503	118	4	h	h	NOUN
eurjchem-503	119	1	o	o	NOUN
eurjchem-503	119	2	n	n	CCONJ
eurjchem-503	119	3	h	h	NOUN
eurjchem-503	119	4	n	n	CCONJ
eurjchem-503	119	5	meo	meo	PROPN
eurjchem-503	119	6	h	h	NOUN
eurjchem-503	119	7	h	h	NOUN
eurjchem-503	120	1	o	o	INTJ
eurjchem-503	120	2	ome	ome	INTJ
eurjchem-503	121	1	n	n	PRON
eurjchem-503	121	2	h	h	NOUN
eurjchem-503	121	3	n	n	CCONJ
eurjchem-503	121	4	meo	meo	PROPN
eurjchem-503	121	5	h	h	PROPN
eurjchem-503	121	6	h	h	PROPN
eurjchem-503	121	7	ome	ome	PROPN
eurjchem-503	122	1	n	n	PRON
eurjchem-503	122	2	h	h	NOUN
eurjchem-503	122	3	n	n	CCONJ
eurjchem-503	122	4	meo	meo	PROPN
eurjchem-503	122	5	h	h	NOUN
eurjchem-503	122	6	h	h	NOUN
eurjchem-503	123	1	o	o	X
eurjchem-503	123	2	(	(	PUNCT
eurjchem-503	123	3	±)-reserpine	±)-reserpine	NUM
eurjchem-503	123	4	n	n	CCONJ
eurjchem-503	123	5	h	h	NOUN
eurjchem-503	123	6	n	n	CCONJ
eurjchem-503	123	7	meo	meo	PROPN
eurjchem-503	123	8	h	h	NOUN
eurjchem-503	123	9	meooc	meooc	NOUN
eurjchem-503	123	10	o	o	INTJ
eurjchem-503	124	1	h	h	NOUN
eurjchem-503	124	2	h	h	NOUN
eurjchem-503	125	1	ome	ome	INTJ
eurjchem-503	125	2	o	o	INTJ
eurjchem-503	125	3	ome	ome	INTJ
eurjchem-503	125	4	ome	ome	INTJ
eurjchem-503	125	5	ome	ome	ADP
eurjchem-503	125	6	a	a	DET
eurjchem-503	125	7	b	b	NOUN
eurjchem-503	125	8	c	c	NOUN
eurjchem-503	125	9	d	d	SYM
eurjchem-503	125	10	9	9	NUM
eurjchem-503	125	11	10	10	NUM
eurjchem-503	125	12	11	11	NUM
eurjchem-503	125	13	12	12	NUM
eurjchem-503	125	14	13	13	NUM
eurjchem-503	125	15	14	14	NUM
eurjchem-503	125	16	e	e	NOUN
eurjchem-503	125	17	a	a	PRON
eurjchem-503	125	18	)	)	PUNCT
eurjchem-503	125	19	lialh4	lialh4	NOUN
eurjchem-503	125	20	(	(	PUNCT
eurjchem-503	125	21	14	14	NUM
eurjchem-503	125	22	eq	eq	NOUN
eurjchem-503	125	23	.	.	PROPN
eurjchem-503	125	24	)	)	PUNCT
eurjchem-503	125	25	,	,	PUNCT
eurjchem-503	125	26	2	2	NUM
eurjchem-503	125	27	h	h	NOUN
eurjchem-503	125	28	reflux	reflux	NOUN
eurjchem-503	125	29	,	,	PUNCT
eurjchem-503	125	30	96	96	NUM
eurjchem-503	125	31	%	%	NOUN
eurjchem-503	125	32	.	.	PUNCT
eurjchem-503	126	1	b	b	X
eurjchem-503	126	2	)	)	PUNCT
eurjchem-503	126	3	10	10	NUM
eurjchem-503	126	4	%	%	NOUN
eurjchem-503	126	5	hcl	hcl	PROPN
eurjchem-503	126	6	,	,	PUNCT
eurjchem-503	126	7	meoh	meoh	PROPN
eurjchem-503	126	8	,	,	PUNCT
eurjchem-503	126	9	1	1	NUM
eurjchem-503	126	10	h	h	NOUN
eurjchem-503	126	11	,	,	PUNCT
eurjchem-503	126	12	rt	rt	PROPN
eurjchem-503	126	13	,	,	PUNCT
eurjchem-503	126	14	98	98	NUM
eurjchem-503	126	15	%	%	NOUN
eurjchem-503	126	16	.	.	PUNCT
eurjchem-503	127	1	c	c	X
eurjchem-503	127	2	)	)	PUNCT
eurjchem-503	127	3	naoh	naoh	NOUN
eurjchem-503	127	4	(	(	PUNCT
eurjchem-503	127	5	4	4	NUM
eurjchem-503	127	6	eq	eq	NOUN
eurjchem-503	127	7	.	.	PROPN
eurjchem-503	127	8	)	)	PUNCT
eurjchem-503	127	9	,	,	PUNCT
eurjchem-503	127	10	meoh	meoh	NOUN
eurjchem-503	127	11	,	,	PUNCT
eurjchem-503	127	12	0	0	NUM
eurjchem-503	127	13	-	-	SYM
eurjchem-503	127	14	5	5	NUM
eurjchem-503	127	15	oc	oc	NOUN
eurjchem-503	127	16	,	,	PUNCT
eurjchem-503	127	17	90	90	NUM
eurjchem-503	127	18	min	min	NOUN
eurjchem-503	127	19	,	,	PUNCT
eurjchem-503	127	20	98	98	NUM
eurjchem-503	127	21	%	%	NOUN
eurjchem-503	127	22	.	.	PUNCT
eurjchem-503	128	1	d	d	X
eurjchem-503	128	2	)	)	PUNCT
eurjchem-503	128	3	35	35	NUM
eurjchem-503	128	4	%	%	NOUN
eurjchem-503	128	5	h2o2	h2o2	NOUN
eurjchem-503	128	6	,	,	PUNCT
eurjchem-503	128	7	naoh	naoh	NOUN
eurjchem-503	128	8	,	,	PUNCT
eurjchem-503	128	9	0	0	NUM
eurjchem-503	128	10	-	-	SYM
eurjchem-503	128	11	5	5	NUM
eurjchem-503	128	12	oc	oc	NOUN
eurjchem-503	128	13	,	,	PUNCT
eurjchem-503	128	14	90	90	NUM
eurjchem-503	128	15	min	min	NOUN
eurjchem-503	128	16	,	,	PUNCT
eurjchem-503	128	17	86	86	NUM
eurjchem-503	128	18	%	%	NOUN
eurjchem-503	128	19	.	.	PUNCT
eurjchem-503	129	1	e	e	X
eurjchem-503	129	2	)	)	PUNCT
eurjchem-503	129	3	conc	conc	NOUN
eurjchem-503	129	4	.	.	PUNCT
eurjchem-503	130	1	h2so4	h2so4	PROPN
eurjchem-503	130	2	,	,	PUNCT
eurjchem-503	130	3	meoh	meoh	PROPN
eurjchem-503	130	4	,	,	PUNCT
eurjchem-503	130	5	reflux	reflux	NOUN
eurjchem-503	130	6	,	,	PUNCT
eurjchem-503	130	7	6	6	NUM
eurjchem-503	130	8	h	h	NOUN
eurjchem-503	130	9	,	,	PUNCT
eurjchem-503	130	10	86	86	NUM
eurjchem-503	130	11	%	%	NOUN
eurjchem-503	130	12	.	.	PUNCT
eurjchem-503	131	1	scheme	scheme	NOUN
eurjchem-503	131	2	3	3	NUM
eurjchem-503	131	3	3.37‐3.25	3.37‐3.25	NUM
eurjchem-503	131	4	(	(	PUNCT
eurjchem-503	131	5	2h	2h	NUM
eurjchem-503	131	6	,	,	PUNCT
eurjchem-503	131	7	m	m	PROPN
eurjchem-503	131	8	,	,	PUNCT
eurjchem-503	131	9	18‐h2	18‐h2	PROPN
eurjchem-503	131	10	)	)	PUNCT
eurjchem-503	131	11	,	,	PUNCT
eurjchem-503	131	12	3.13	3.13	NUM
eurjchem-503	131	13	(	(	PUNCT
eurjchem-503	131	14	1h	1h	NUM
eurjchem-503	131	15	,	,	PUNCT
eurjchem-503	131	16	brd	brd	PROPN
eurjchem-503	131	17	,	,	PUNCT
eurjchem-503	131	18	j	j	PROPN
eurjchem-503	132	1	=	=	PROPN
eurjchem-503	132	2	12	12	NUM
eurjchem-503	132	3	hz	hz	VERB
eurjchem-503	132	4	,	,	PUNCT
eurjchem-503	132	5	3‐h	3‐h	NUM
eurjchem-503	132	6	)	)	PUNCT
eurjchem-503	132	7	,	,	PUNCT
eurjchem-503	132	8	2.79	2.79	NUM
eurjchem-503	132	9	(	(	PUNCT
eurjchem-503	132	10	1h	1h	NUM
eurjchem-503	132	11	,	,	PUNCT
eurjchem-503	132	12	brd	brd	PROPN
eurjchem-503	132	13	,	,	PUNCT
eurjchem-503	132	14	j	j	PROPN
eurjchem-503	133	1	=	=	SYM
eurjchem-503	133	2	13	13	NUM
eurjchem-503	133	3	and	and	CCONJ
eurjchem-503	133	4	3.5	3.5	NUM
eurjchem-503	133	5	hz	hz	NOUN
eurjchem-503	133	6	,	,	PUNCT
eurjchem-503	133	7	16‐h	16‐h	NUM
eurjchem-503	133	8	)	)	PUNCT
eurjchem-503	133	9	,	,	PUNCT
eurjchem-503	133	10	2.62‐2.54	2.62‐2.54	NUM
eurjchem-503	133	11	(	(	PUNCT
eurjchem-503	133	12	4h	4h	NUM
eurjchem-503	133	13	,	,	PUNCT
eurjchem-503	133	14	m	m	PROPN
eurjchem-503	133	15	,	,	PUNCT
eurjchem-503	133	16	6‐h2	6‐h2	NUM
eurjchem-503	133	17	,	,	PUNCT
eurjchem-503	133	18	and	and	CCONJ
eurjchem-503	134	1	5‐	5‐	NUM
eurjchem-503	134	2	h2	h2	NOUN
eurjchem-503	134	3	)	)	PUNCT
eurjchem-503	134	4	,	,	PUNCT
eurjchem-503	134	5	2.51	2.51	NUM
eurjchem-503	134	6	(	(	PUNCT
eurjchem-503	134	7	1h	1h	NUM
eurjchem-503	134	8	,	,	PUNCT
eurjchem-503	134	9	dd	dd	NOUN
eurjchem-503	134	10	,	,	PUNCT
eurjchem-503	134	11	j	j	PROPN
eurjchem-503	134	12	=	=	SYM
eurjchem-503	134	13	15	15	NUM
eurjchem-503	134	14	and	and	CCONJ
eurjchem-503	134	15	5	5	NUM
eurjchem-503	134	16	hz	hz	NOUN
eurjchem-503	134	17	,	,	PUNCT
eurjchem-503	134	18	16‐h	16‐h	NUM
eurjchem-503	134	19	)	)	PUNCT
eurjchem-503	134	20	,	,	PUNCT
eurjchem-503	134	21	2.35	2.35	NUM
eurjchem-503	134	22	(	(	PUNCT
eurjchem-503	134	23	1h	1h	NUM
eurjchem-503	134	24	,	,	PUNCT
eurjchem-503	134	25	ddd	ddd	PROPN
eurjchem-503	134	26	,	,	PUNCT
eurjchem-503	134	27	j	j	PROPN
eurjchem-503	135	1	=	=	PROPN
eurjchem-503	135	2	12	12	NUM
eurjchem-503	135	3	,	,	PUNCT
eurjchem-503	135	4	4.5	4.5	NUM
eurjchem-503	135	5	,	,	PUNCT
eurjchem-503	135	6	and	and	CCONJ
eurjchem-503	135	7	2.5	2.5	NUM
eurjchem-503	135	8	hz	hz	NOUN
eurjchem-503	135	9	,	,	PUNCT
eurjchem-503	135	10	14‐heq	14‐heq	NUM
eurjchem-503	135	11	)	)	PUNCT
eurjchem-503	135	12	,	,	PUNCT
eurjchem-503	135	13	2.27‐2.20	2.27‐2.20	NUM
eurjchem-503	135	14	(	(	PUNCT
eurjchem-503	135	15	1h	1h	NUM
eurjchem-503	135	16	,	,	PUNCT
eurjchem-503	135	17	m	m	PROPN
eurjchem-503	135	18	,	,	PUNCT
eurjchem-503	135	19	15‐h	15‐h	NUM
eurjchem-503	135	20	)	)	PUNCT
eurjchem-503	135	21	,	,	PUNCT
eurjchem-503	135	22	and	and	CCONJ
eurjchem-503	135	23	2.18	2.18	NUM
eurjchem-503	135	24	(	(	PUNCT
eurjchem-503	135	25	1h	1h	NUM
eurjchem-503	135	26	,	,	PUNCT
eurjchem-503	135	27	q	q	NOUN
eurjchem-503	135	28	,	,	PUNCT
eurjchem-503	135	29	j	j	PROPN
eurjchem-503	135	30	=	=	PROPN
eurjchem-503	135	31	12	12	NUM
eurjchem-503	135	32	hz	hz	VERB
eurjchem-503	135	33	,	,	PUNCT
eurjchem-503	135	34	14‐hax	14‐hax	NUM
eurjchem-503	135	35	)	)	PUNCT
eurjchem-503	135	36	.	.	PUNCT
eurjchem-503	136	1	ms	ms	PROPN
eurjchem-503	136	2	m	m	PROPN
eurjchem-503	136	3	/	/	SYM
eurjchem-503	136	4	z	z	PROPN
eurjchem-503	136	5	(	(	PUNCT
eurjchem-503	136	6	ei	ei	NOUN
eurjchem-503	136	7	)	)	PUNCT
eurjchem-503	136	8	322	322	NUM
eurjchem-503	136	9	;	;	PUNCT
eurjchem-503	137	1	hrms	hrm	VERB
eurjchem-503	137	2	calcd	calcd	NOUN
eurjchem-503	137	3	.	.	PUNCT
eurjchem-503	138	1	for	for	ADP
eurjchem-503	138	2	c20h22n2o2	c20h22n2o2	NOUN
eurjchem-503	138	3	(	(	PUNCT
eurjchem-503	138	4	m+	m+	NUM
eurjchem-503	138	5	):	):	PUNCT
eurjchem-503	138	6	322.1681	322.1681	NUM
eurjchem-503	138	7	,	,	PUNCT
eurjchem-503	138	8	found	find	VERB
eurjchem-503	138	9	:	:	PUNCT
eurjchem-503	139	1	322.1681	322.1681	X
eurjchem-503	139	2	.	.	PUNCT
eurjchem-503	140	1	2.2.8	2.2.8	NUM
eurjchem-503	140	2	.	.	PUNCT
eurjchem-503	141	1	11‐methoxy‐(20α	11‐methoxy‐(20α	X
eurjchem-503	141	2	)	)	PUNCT
eurjchem-503	141	3	18,19‐didehydroyohimban‐17‐one	18,19‐didehydroyohimban‐17‐one	NOUN
eurjchem-503	141	4	(	(	PUNCT
eurjchem-503	141	5	12	12	NUM
eurjchem-503	141	6	)	)	PUNCT
eurjchem-503	141	7	a	a	DET
eurjchem-503	141	8	solution	solution	NOUN
eurjchem-503	141	9	of	of	ADP
eurjchem-503	141	10	sodium	sodium	NOUN
eurjchem-503	141	11	hydroxide	hydroxide	NOUN
eurjchem-503	141	12	(	(	PUNCT
eurjchem-503	141	13	100	100	NUM
eurjchem-503	141	14	mg	mg	NOUN
eurjchem-503	141	15	,	,	PUNCT
eurjchem-503	141	16	2.50	2.50	NUM
eurjchem-503	141	17	mmol	mmol	NOUN
eurjchem-503	141	18	)	)	PUNCT
eurjchem-503	141	19	in	in	ADP
eurjchem-503	141	20	methanol	methanol	NOUN
eurjchem-503	141	21	(	(	PUNCT
eurjchem-503	141	22	1	1	NUM
eurjchem-503	141	23	ml	ml	NOUN
eurjchem-503	141	24	)	)	PUNCT
eurjchem-503	141	25	was	be	AUX
eurjchem-503	141	26	added	add	VERB
eurjchem-503	141	27	to	to	ADP
eurjchem-503	141	28	an	an	DET
eurjchem-503	141	29	ice‐cooled	ice‐coole	VERB
eurjchem-503	141	30	,	,	PUNCT
eurjchem-503	141	31	stirred	stir	VERB
eurjchem-503	141	32	solution	solution	NOUN
eurjchem-503	141	33	of	of	ADP
eurjchem-503	141	34	the	the	DET
eurjchem-503	141	35	enone	enone	NOUN
eurjchem-503	141	36	,	,	PUNCT
eurjchem-503	141	37	11	11	NUM
eurjchem-503	141	38	,	,	PUNCT
eurjchem-503	141	39	(	(	PUNCT
eurjchem-503	141	40	200	200	NUM
eurjchem-503	141	41	mg	mg	NOUN
eurjchem-503	141	42	,	,	PUNCT
eurjchem-503	141	43	0.621	0.621	NUM
eurjchem-503	141	44	mmol	mmol	NOUN
eurjchem-503	141	45	)	)	PUNCT
eurjchem-503	141	46	in	in	ADP
eurjchem-503	141	47	a	a	DET
eurjchem-503	141	48	mixture	mixture	NOUN
eurjchem-503	141	49	of	of	ADP
eurjchem-503	141	50	methanol	methanol	NOUN
eurjchem-503	141	51	:	:	PUNCT
eurjchem-503	141	52	methylene	methylene	NOUN
eurjchem-503	141	53	dichloride	dichloride	NOUN
eurjchem-503	141	54	(	(	PUNCT
eurjchem-503	141	55	4:1	4:1	NUM
eurjchem-503	141	56	)	)	PUNCT
eurjchem-503	141	57	(	(	PUNCT
eurjchem-503	141	58	20	20	NUM
eurjchem-503	141	59	ml	ml	NOUN
eurjchem-503	141	60	)	)	PUNCT
eurjchem-503	141	61	under	under	ADP
eurjchem-503	141	62	argon	argon	NOUN
eurjchem-503	141	63	stream	stream	NOUN
eurjchem-503	141	64	.	.	PUNCT
eurjchem-503	142	1	after	after	ADP
eurjchem-503	142	2	being	be	AUX
eurjchem-503	142	3	stirred	stir	VERB
eurjchem-503	142	4	under	under	ADP
eurjchem-503	142	5	ice‐cooling	ice‐coole	VERB
eurjchem-503	142	6	for	for	ADP
eurjchem-503	142	7	1	1	NUM
eurjchem-503	142	8	and	and	CCONJ
eurjchem-503	142	9	half	half	ADJ
eurjchem-503	142	10	hours	hour	NOUN
eurjchem-503	142	11	,	,	PUNCT
eurjchem-503	142	12	the	the	DET
eurjchem-503	142	13	reaction	reaction	NOUN
eurjchem-503	142	14	mixture	mixture	NOUN
eurjchem-503	142	15	was	be	AUX
eurjchem-503	142	16	diluted	dilute	VERB
eurjchem-503	142	17	with	with	ADP
eurjchem-503	142	18	water	water	NOUN
eurjchem-503	142	19	and	and	CCONJ
eurjchem-503	142	20	extracted	extract	VERB
eurjchem-503	142	21	with	with	ADP
eurjchem-503	142	22	methylene	methylene	ADJ
eurjchem-503	142	23	dichloride	dichloride	NOUN
eurjchem-503	142	24	.	.	PUNCT
eurjchem-503	143	1	the	the	DET
eurjchem-503	143	2	extract	extract	NOUN
eurjchem-503	143	3	was	be	AUX
eurjchem-503	143	4	washed	wash	VERB
eurjchem-503	143	5	,	,	PUNCT
eurjchem-503	143	6	dried	dry	VERB
eurjchem-503	143	7	,	,	PUNCT
eurjchem-503	143	8	and	and	CCONJ
eurjchem-503	143	9	evaporated	evaporate	VERB
eurjchem-503	143	10	to	to	PART
eurjchem-503	143	11	give	give	VERB
eurjchem-503	143	12	a	a	DET
eurjchem-503	143	13	solid	solid	NOUN
eurjchem-503	143	14	,	,	PUNCT
eurjchem-503	143	15	which	which	PRON
eurjchem-503	143	16	was	be	AUX
eurjchem-503	143	17	recrystallized	recrystallize	VERB
eurjchem-503	143	18	from	from	ADP
eurjchem-503	143	19	methanol	methanol	NOUN
eurjchem-503	143	20	to	to	PART
eurjchem-503	143	21	afford	afford	VERB
eurjchem-503	143	22	the	the	DET
eurjchem-503	143	23	cis‐enone	cis‐enone	NOUN
eurjchem-503	143	24	,	,	PUNCT
eurjchem-503	143	25	12	12	NUM
eurjchem-503	143	26	,	,	PUNCT
eurjchem-503	143	27	as	as	ADP
eurjchem-503	143	28	colorless	colorless	ADJ
eurjchem-503	143	29	crystals	crystal	NOUN
eurjchem-503	143	30	(	(	PUNCT
eurjchem-503	143	31	scheme	scheme	NOUN
eurjchem-503	143	32	3	3	NUM
eurjchem-503	143	33	)	)	PUNCT
eurjchem-503	143	34	.	.	PUNCT
eurjchem-503	144	1	m.p	m.p	PROPN
eurjchem-503	144	2	.	.	PROPN
eurjchem-503	144	3	:	:	PUNCT
eurjchem-503	145	1	188‐190	188‐190	NUM
eurjchem-503	145	2	oc	oc	PROPN
eurjchem-503	145	3	.	.	PROPN
eurjchem-503	145	4	yield	yield	NOUN
eurjchem-503	145	5	:	:	PUNCT
eurjchem-503	145	6	196	196	NUM
eurjchem-503	145	7	mg	mg	NOUN
eurjchem-503	145	8	,	,	PUNCT
eurjchem-503	145	9	98	98	NUM
eurjchem-503	145	10	%	%	NOUN
eurjchem-503	145	11	.	.	PUNCT
eurjchem-503	146	1	ir	ir	PROPN
eurjchem-503	146	2	(	(	PUNCT
eurjchem-503	146	3	max	max	PROPN
eurjchem-503	146	4	,	,	PUNCT
eurjchem-503	146	5	thin	thin	ADJ
eurjchem-503	146	6	film	film	NOUN
eurjchem-503	146	7	,	,	PUNCT
eurjchem-503	146	8	cm‐1	cm‐1	PROPN
eurjchem-503	146	9	):	):	PUNCT
eurjchem-503	146	10	3374	3374	NUM
eurjchem-503	146	11	(	(	PUNCT
eurjchem-503	146	12	nh	nh	NOUN
eurjchem-503	146	13	)	)	PUNCT
eurjchem-503	146	14	,	,	PUNCT
eurjchem-503	146	15	1662	1662	NUM
eurjchem-503	146	16	(	(	PUNCT
eurjchem-503	146	17	c	c	NOUN
eurjchem-503	146	18	=	=	NOUN
eurjchem-503	146	19	o	o	NOUN
eurjchem-503	146	20	)	)	PUNCT
eurjchem-503	146	21	.	.	PUNCT
eurjchem-503	147	1	1h	1h	NUM
eurjchem-503	147	2	nmr	nmr	NOUN
eurjchem-503	147	3	(	(	PUNCT
eurjchem-503	147	4	400	400	NUM
eurjchem-503	147	5	mhz	mhz	NOUN
eurjchem-503	147	6	,	,	PUNCT
eurjchem-503	147	7	cdcl3	cdcl3	NOUN
eurjchem-503	147	8	,	,	PUNCT
eurjchem-503	147	9			NUM
eurjchem-503	147	10	,	,	PUNCT
eurjchem-503	147	11	ppm	ppm	NUM
eurjchem-503	147	12	):	):	PUNCT
eurjchem-503	147	13	7.75	7.75	NUM
eurjchem-503	147	14	(	(	PUNCT
eurjchem-503	147	15	1h	1h	NUM
eurjchem-503	147	16	,	,	PUNCT
eurjchem-503	147	17	s	s	X
eurjchem-503	147	18	,	,	PUNCT
eurjchem-503	147	19	nh	nh	PROPN
eurjchem-503	147	20	)	)	PUNCT
eurjchem-503	147	21	,	,	PUNCT
eurjchem-503	147	22	7.41	7.41	NUM
eurjchem-503	147	23	(	(	PUNCT
eurjchem-503	147	24	1h	1h	NUM
eurjchem-503	147	25	,	,	PUNCT
eurjchem-503	147	26	d	d	PROPN
eurjchem-503	147	27	,	,	PUNCT
eurjchem-503	147	28	j	j	PROPN
eurjchem-503	147	29	=	=	SYM
eurjchem-503	147	30	8.3	8.3	NUM
eurjchem-503	147	31	hz	hz	VERB
eurjchem-503	147	32	,	,	PUNCT
eurjchem-503	147	33	9‐h	9‐h	NOUN
eurjchem-503	147	34	)	)	PUNCT
eurjchem-503	147	35	,	,	PUNCT
eurjchem-503	147	36	6.87	6.87	NUM
eurjchem-503	147	37	(	(	PUNCT
eurjchem-503	147	38	1h	1h	NUM
eurjchem-503	147	39	,	,	PUNCT
eurjchem-503	147	40	d	d	PROPN
eurjchem-503	147	41	,	,	PUNCT
eurjchem-503	147	42	2.2	2.2	NUM
eurjchem-503	147	43	hz	hz	NOUN
eurjchem-503	147	44	,	,	PUNCT
eurjchem-503	147	45	12‐h	12‐h	NUM
eurjchem-503	147	46	)	)	PUNCT
eurjchem-503	147	47	,	,	PUNCT
eurjchem-503	147	48	6.78	6.78	NUM
eurjchem-503	147	49	(	(	PUNCT
eurjchem-503	147	50	1h	1h	NUM
eurjchem-503	147	51	,	,	PUNCT
eurjchem-503	147	52	dd	dd	NOUN
eurjchem-503	147	53	,	,	PUNCT
eurjchem-503	147	54	j	j	PROPN
eurjchem-503	147	55	=	=	NOUN
eurjchem-503	147	56	8.3	8.3	NUM
eurjchem-503	147	57	,	,	PUNCT
eurjchem-503	147	58	2.2	2.2	NUM
eurjchem-503	147	59	hz	hz	NOUN
eurjchem-503	147	60	,	,	PUNCT
eurjchem-503	147	61	10‐h	10‐h	NUM
eurjchem-503	147	62	)	)	PUNCT
eurjchem-503	147	63	,	,	PUNCT
eurjchem-503	147	64	6.43	6.43	NUM
eurjchem-503	147	65	(	(	PUNCT
eurjchem-503	147	66	1h	1h	NUM
eurjchem-503	147	67	,	,	PUNCT
eurjchem-503	147	68	dt	dt	PROPN
eurjchem-503	147	69	,	,	PUNCT
eurjchem-503	147	70	j	j	PROPN
eurjchem-503	148	1	=	=	NOUN
eurjchem-503	148	2	10.1	10.1	NUM
eurjchem-503	148	3	and	and	CCONJ
eurjchem-503	148	4	1.9	1.9	NUM
eurjchem-503	148	5	hz	hz	NOUN
eurjchem-503	148	6	,	,	PUNCT
eurjchem-503	148	7	19‐h	19‐h	NUM
eurjchem-503	148	8	)	)	PUNCT
eurjchem-503	148	9	,	,	PUNCT
eurjchem-503	148	10	5.98	5.98	NUM
eurjchem-503	148	11	(	(	PUNCT
eurjchem-503	148	12	1h	1h	NUM
eurjchem-503	148	13	,	,	PUNCT
eurjchem-503	148	14	dd	dd	NOUN
eurjchem-503	148	15	,	,	PUNCT
eurjchem-503	148	16	j	j	PROPN
eurjchem-503	149	1	=	=	NOUN
eurjchem-503	149	2	10.1	10.1	NUM
eurjchem-503	149	3	and	and	CCONJ
eurjchem-503	149	4	2.3	2.3	NUM
eurjchem-503	149	5	hz	hz	NOUN
eurjchem-503	149	6	,	,	PUNCT
eurjchem-503	149	7	18‐h	18‐h	NUM
eurjchem-503	149	8	)	)	PUNCT
eurjchem-503	149	9	,	,	PUNCT
eurjchem-503	149	10	3.79	3.79	NUM
eurjchem-503	149	11	(	(	PUNCT
eurjchem-503	149	12	3h	3h	NUM
eurjchem-503	149	13	,	,	PUNCT
eurjchem-503	149	14	s	s	X
eurjchem-503	149	15	,	,	PUNCT
eurjchem-503	149	16	ome	ome	PROPN
eurjchem-503	149	17	)	)	PUNCT
eurjchem-503	149	18	,	,	PUNCT
eurjchem-503	149	19	3.22‐3.16	3.22‐3.16	PROPN
eurjchem-503	149	20	(	(	PUNCT
eurjchem-503	149	21	2h	2h	NUM
eurjchem-503	149	22	,	,	PUNCT
eurjchem-503	149	23	m	m	PROPN
eurjchem-503	149	24	,	,	PUNCT
eurjchem-503	149	25	21‐h2	21‐h2	PROPN
eurjchem-503	149	26	)	)	PUNCT
eurjchem-503	149	27	,	,	PUNCT
eurjchem-503	149	28	3.42	3.42	NUM
eurjchem-503	149	29	(	(	PUNCT
eurjchem-503	149	30	1h	1h	NUM
eurjchem-503	149	31	,	,	PUNCT
eurjchem-503	149	32	brd	brd	PROPN
eurjchem-503	149	33	,	,	PUNCT
eurjchem-503	149	34	j	j	PROPN
eurjchem-503	149	35	=	=	PROPN
eurjchem-503	149	36	12	12	NUM
eurjchem-503	149	37	hz	hz	VERB
eurjchem-503	149	38	,	,	PUNCT
eurjchem-503	149	39	3‐h	3‐h	NUM
eurjchem-503	149	40	)	)	PUNCT
eurjchem-503	149	41	,	,	PUNCT
eurjchem-503	149	42	2.91	2.91	NUM
eurjchem-503	149	43	(	(	PUNCT
eurjchem-503	149	44	1h	1h	NUM
eurjchem-503	149	45	,	,	PUNCT
eurjchem-503	149	46	brs	br	VERB
eurjchem-503	149	47	,	,	PUNCT
eurjchem-503	149	48	20‐h	20‐h	NUM
eurjchem-503	149	49	)	)	PUNCT
eurjchem-503	149	50	,	,	PUNCT
eurjchem-503	149	51	2.86	2.86	NUM
eurjchem-503	149	52	(	(	PUNCT
eurjchem-503	149	53	1h	1h	NUM
eurjchem-503	149	54	,	,	PUNCT
eurjchem-503	149	55	brd	brd	PROPN
eurjchem-503	149	56	,	,	PUNCT
eurjchem-503	149	57	j	j	PROPN
eurjchem-503	149	58	=	=	SYM
eurjchem-503	149	59	13	13	NUM
eurjchem-503	149	60	and	and	CCONJ
eurjchem-503	149	61	3.5	3.5	NUM
eurjchem-503	149	62	hz	hz	NOUN
eurjchem-503	149	63	,	,	PUNCT
eurjchem-503	149	64	16‐h	16‐h	NUM
eurjchem-503	149	65	)	)	PUNCT
eurjchem-503	149	66	,	,	PUNCT
eurjchem-503	149	67	2.82	2.82	NUM
eurjchem-503	149	68	(	(	PUNCT
eurjchem-503	149	69	1h	1h	NUM
eurjchem-503	149	70	,	,	PUNCT
eurjchem-503	149	71	dt	dt	PROPN
eurjchem-503	149	72	,	,	PUNCT
eurjchem-503	149	73	j	j	PROPN
eurjchem-503	149	74	=	=	PROPN
eurjchem-503	149	75	12	12	NUM
eurjchem-503	149	76	and	and	CCONJ
eurjchem-503	149	77	5.5	5.5	NUM
eurjchem-503	149	78	hz	hz	NOUN
eurjchem-503	149	79	,	,	PUNCT
eurjchem-503	149	80	14‐heq	14‐heq	NUM
eurjchem-503	149	81	)	)	PUNCT
eurjchem-503	149	82	,	,	PUNCT
eurjchem-503	149	83	2.67	2.67	NUM
eurjchem-503	149	84	(	(	PUNCT
eurjchem-503	149	85	1h	1h	NUM
eurjchem-503	149	86	,	,	PUNCT
eurjchem-503	149	87	dd	dd	NOUN
eurjchem-503	149	88	,	,	PUNCT
eurjchem-503	149	89	j	j	PROPN
eurjchem-503	149	90	=	=	SYM
eurjchem-503	149	91	15	15	NUM
eurjchem-503	149	92	and	and	CCONJ
eurjchem-503	149	93	5	5	NUM
eurjchem-503	149	94	hz	hz	NOUN
eurjchem-503	149	95	,	,	PUNCT
eurjchem-503	149	96	16‐h	16‐h	NUM
eurjchem-503	149	97	)	)	PUNCT
eurjchem-503	149	98	,	,	PUNCT
eurjchem-503	149	99	2.57‐2.48	2.57‐2.48	NUM
eurjchem-503	149	100	(	(	PUNCT
eurjchem-503	149	101	4h	4h	NUM
eurjchem-503	149	102	,	,	PUNCT
eurjchem-503	149	103	m	m	PROPN
eurjchem-503	149	104	,	,	PUNCT
eurjchem-503	149	105	6‐h2	6‐h2	NUM
eurjchem-503	149	106	,	,	PUNCT
eurjchem-503	149	107	and	and	CCONJ
eurjchem-503	149	108	5‐h2	5‐h2	NUM
eurjchem-503	149	109	)	)	PUNCT
eurjchem-503	149	110	,	,	PUNCT
eurjchem-503	149	111	2.29‐2.22	2.29‐2.22	NUM
eurjchem-503	149	112	(	(	PUNCT
eurjchem-503	149	113	1h	1h	NUM
eurjchem-503	149	114	,	,	PUNCT
eurjchem-503	149	115	m	m	PROPN
eurjchem-503	149	116	,	,	PUNCT
eurjchem-503	149	117	15‐h	15‐h	NUM
eurjchem-503	149	118	)	)	PUNCT
eurjchem-503	149	119	,	,	PUNCT
eurjchem-503	149	120	2.08	2.08	NUM
eurjchem-503	149	121	(	(	PUNCT
eurjchem-503	149	122	1h	1h	NUM
eurjchem-503	149	123	,	,	PUNCT
eurjchem-503	149	124	ddd	ddd	PROPN
eurjchem-503	149	125	,	,	PUNCT
eurjchem-503	149	126	j	j	NOUN
eurjchem-503	149	127	=	=	PROPN
eurjchem-503	149	128	12.5	12.5	NUM
eurjchem-503	149	129	,	,	PUNCT
eurjchem-503	149	130	11.8	11.8	NUM
eurjchem-503	149	131	and	and	CCONJ
eurjchem-503	149	132	10.5	10.5	NUM
eurjchem-503	149	133	hz	hz	NOUN
eurjchem-503	149	134	,	,	PUNCT
eurjchem-503	149	135	14‐	14‐	NUM
eurjchem-503	149	136	hax	hax	NOUN
eurjchem-503	149	137	)	)	PUNCT
eurjchem-503	149	138	.	.	PUNCT
eurjchem-503	150	1	ms	ms	NOUN
eurjchem-503	150	2	(	(	PUNCT
eurjchem-503	150	3	m	m	PROPN
eurjchem-503	150	4	/	/	SYM
eurjchem-503	150	5	z	z	NOUN
eurjchem-503	150	6	,	,	PUNCT
eurjchem-503	150	7	ei	ei	PROPN
eurjchem-503	150	8	):	):	PUNCT
eurjchem-503	150	9	322	322	NUM
eurjchem-503	150	10	;	;	PUNCT
eurjchem-503	150	11	hrms	hrm	VERB
eurjchem-503	150	12	calcd	calcd	NOUN
eurjchem-503	150	13	.	.	PUNCT
eurjchem-503	151	1	for	for	ADP
eurjchem-503	151	2	c20h22n2o2	c20h22n2o2	NOUN
eurjchem-503	151	3	(	(	PUNCT
eurjchem-503	151	4	m+	m+	NUM
eurjchem-503	151	5	):	):	PUNCT
eurjchem-503	151	6	322.1681	322.1681	NUM
eurjchem-503	151	7	,	,	PUNCT
eurjchem-503	151	8	found	find	VERB
eurjchem-503	151	9	:	:	PUNCT
eurjchem-503	151	10	322.1678	322.1678	NUM
eurjchem-503	151	11	.	.	NOUN
eurjchem-503	152	1	2.2.9	2.2.9	NUM
eurjchem-503	152	2	.	.	PUNCT
eurjchem-503	153	1	11‐methoxy‐(18α	11‐methoxy‐(18α	NUM
eurjchem-503	153	2	,	,	PUNCT
eurjchem-503	153	3	19α	19α	NUM
eurjchem-503	153	4	,	,	PUNCT
eurjchem-503	153	5	20α)‐18,19‐epoxy‐yohimban‐	20α)‐18,19‐epoxy‐yohimban‐	NUM
eurjchem-503	153	6	17‐one	17‐one	NUM
eurjchem-503	153	7	(	(	PUNCT
eurjchem-503	153	8	13	13	NUM
eurjchem-503	153	9	)	)	PUNCT
eurjchem-503	153	10	hydrogen	hydrogen	NOUN
eurjchem-503	153	11	peroxide	peroxide	NOUN
eurjchem-503	153	12	(	(	PUNCT
eurjchem-503	153	13	35	35	NUM
eurjchem-503	153	14	%	%	NOUN
eurjchem-503	153	15	,	,	PUNCT
eurjchem-503	153	16	8	8	NUM
eurjchem-503	153	17	ml	ml	NOUN
eurjchem-503	153	18	)	)	PUNCT
eurjchem-503	153	19	and	and	CCONJ
eurjchem-503	153	20	10	10	NUM
eurjchem-503	153	21	%	%	NOUN
eurjchem-503	153	22	methanolic	methanolic	NOUN
eurjchem-503	153	23	sodium	sodium	NOUN
eurjchem-503	153	24	hydroxide	hydroxide	NOUN
eurjchem-503	153	25	solution	solution	NOUN
eurjchem-503	153	26	(	(	PUNCT
eurjchem-503	153	27	2.5	2.5	NUM
eurjchem-503	153	28	ml	ml	NOUN
eurjchem-503	153	29	)	)	PUNCT
eurjchem-503	153	30	were	be	AUX
eurjchem-503	153	31	successively	successively	ADV
eurjchem-503	153	32	added	add	VERB
eurjchem-503	153	33	to	to	ADP
eurjchem-503	153	34	a	a	DET
eurjchem-503	153	35	solution	solution	NOUN
eurjchem-503	153	36	of	of	ADP
eurjchem-503	153	37	the	the	DET
eurjchem-503	153	38	conjugated	conjugated	ADJ
eurjchem-503	153	39	enone	enone	NOUN
eurjchem-503	153	40	,	,	PUNCT
eurjchem-503	153	41	12	12	NUM
eurjchem-503	153	42	,	,	PUNCT
eurjchem-503	153	43	(	(	PUNCT
eurjchem-503	153	44	200	200	NUM
eurjchem-503	153	45	mg	mg	NOUN
eurjchem-503	153	46	,	,	PUNCT
eurjchem-503	153	47	0.621	0.621	NUM
eurjchem-503	153	48	)	)	PUNCT
eurjchem-503	153	49	in	in	ADP
eurjchem-503	153	50	methanol	methanol	NOUN
eurjchem-503	153	51	(	(	PUNCT
eurjchem-503	153	52	8	8	NUM
eurjchem-503	153	53	ml	ml	NOUN
eurjchem-503	153	54	)	)	PUNCT
eurjchem-503	153	55	and	and	CCONJ
eurjchem-503	153	56	methylene	methylene	NOUN
eurjchem-503	153	57	dichloride	dichloride	NOUN
eurjchem-503	153	58	(	(	PUNCT
eurjchem-503	153	59	2	2	NUM
eurjchem-503	153	60	ml	ml	NOUN
eurjchem-503	153	61	)	)	PUNCT
eurjchem-503	153	62	with	with	ADP
eurjchem-503	153	63	stirring	stir	VERB
eurjchem-503	153	64	under	under	ADP
eurjchem-503	153	65	ice	ice	NOUN
eurjchem-503	153	66	cooling	cooling	NOUN
eurjchem-503	153	67	in	in	ADP
eurjchem-503	153	68	argon	argon	NOUN
eurjchem-503	153	69	atmosphere	atmosphere	NOUN
eurjchem-503	153	70	.	.	PUNCT
eurjchem-503	154	1	stirring	stirring	NOUN
eurjchem-503	154	2	was	be	AUX
eurjchem-503	154	3	continued	continue	VERB
eurjchem-503	154	4	at	at	ADP
eurjchem-503	154	5	0	0	NUM
eurjchem-503	154	6	oc	oc	NOUN
eurjchem-503	154	7	for	for	ADP
eurjchem-503	154	8	one	one	NUM
eurjchem-503	154	9	and	and	CCONJ
eurjchem-503	154	10	half	half	ADJ
eurjchem-503	154	11	hours	hour	NOUN
eurjchem-503	154	12	.	.	PUNCT
eurjchem-503	155	1	water	water	NOUN
eurjchem-503	155	2	was	be	AUX
eurjchem-503	155	3	added	add	VERB
eurjchem-503	155	4	to	to	ADP
eurjchem-503	155	5	the	the	DET
eurjchem-503	155	6	reaction	reaction	NOUN
eurjchem-503	155	7	mixture	mixture	NOUN
eurjchem-503	155	8	,	,	PUNCT
eurjchem-503	155	9	which	which	PRON
eurjchem-503	155	10	was	be	AUX
eurjchem-503	155	11	extracted	extract	VERB
eurjchem-503	155	12	with	with	ADP
eurjchem-503	155	13	methylene	methylene	ADJ
eurjchem-503	155	14	dichloride	dichloride	NOUN
eurjchem-503	155	15	.	.	PUNCT
eurjchem-503	156	1	the	the	DET
eurjchem-503	156	2	extract	extract	NOUN
eurjchem-503	156	3	was	be	AUX
eurjchem-503	156	4	washed	wash	VERB
eurjchem-503	156	5	with	with	ADP
eurjchem-503	156	6	brine	brine	NOUN
eurjchem-503	156	7	,	,	PUNCT
eurjchem-503	156	8	dried	dry	VERB
eurjchem-503	156	9	,	,	PUNCT
eurjchem-503	156	10	and	and	CCONJ
eurjchem-503	156	11	evaporated	evaporate	VERB
eurjchem-503	156	12	to	to	PART
eurjchem-503	156	13	give	give	VERB
eurjchem-503	156	14	a	a	DET
eurjchem-503	156	15	brownish	brownish	ADJ
eurjchem-503	156	16	solid	solid	NOUN
eurjchem-503	156	17	,	,	PUNCT
eurjchem-503	156	18	which	which	PRON
eurjchem-503	156	19	was	be	AUX
eurjchem-503	156	20	recrystallized	recrystallize	VERB
eurjchem-503	156	21	from	from	ADP
eurjchem-503	156	22	ethanol	ethanol	NOUN
eurjchem-503	156	23	to	to	PART
eurjchem-503	156	24	afford	afford	VERB
eurjchem-503	156	25	on	on	ADP
eurjchem-503	156	26	the	the	DET
eurjchem-503	156	27	epoxyketone	epoxyketone	PROPN
eurjchem-503	156	28	13	13	NUM
eurjchem-503	156	29	as	as	ADP
eurjchem-503	156	30	white	white	ADJ
eurjchem-503	156	31	crystals	crystal	NOUN
eurjchem-503	156	32	(	(	PUNCT
eurjchem-503	156	33	scheme	scheme	NOUN
eurjchem-503	156	34	3	3	NUM
eurjchem-503	156	35	)	)	PUNCT
eurjchem-503	156	36	.	.	PUNCT
eurjchem-503	157	1	m.p	m.p	PROPN
eurjchem-503	157	2	.	.	PROPN
eurjchem-503	157	3	:	:	PUNCT
eurjchem-503	158	1	203‐	203‐	NUM
eurjchem-503	158	2	205	205	NUM
eurjchem-503	158	3	oc	oc	NOUN
eurjchem-503	158	4	.	.	NOUN
eurjchem-503	158	5	yield	yield	NOUN
eurjchem-503	158	6	:	:	PUNCT
eurjchem-503	158	7	180	180	NUM
eurjchem-503	158	8	mg	mg	NOUN
eurjchem-503	158	9	,	,	PUNCT
eurjchem-503	158	10	86	86	NUM
eurjchem-503	158	11	%	%	NOUN
eurjchem-503	158	12	.	.	PUNCT
eurjchem-503	159	1	ir	ir	PROPN
eurjchem-503	159	2	(	(	PUNCT
eurjchem-503	159	3	max	max	PROPN
eurjchem-503	159	4	,	,	PUNCT
eurjchem-503	159	5	thin	thin	ADJ
eurjchem-503	159	6	film	film	NOUN
eurjchem-503	159	7	,	,	PUNCT
eurjchem-503	159	8	cm‐1	cm‐1	PROPN
eurjchem-503	159	9	):	):	PUNCT
eurjchem-503	159	10	1712	1712	NUM
eurjchem-503	159	11	(	(	PUNCT
eurjchem-503	159	12	c	c	NOUN
eurjchem-503	159	13	=	=	NOUN
eurjchem-503	159	14	o	o	NOUN
eurjchem-503	159	15	)	)	PUNCT
eurjchem-503	159	16	.	.	PUNCT
eurjchem-503	160	1	1h	1h	NUM
eurjchem-503	160	2	nmr	nmr	NOUN
eurjchem-503	160	3	(	(	PUNCT
eurjchem-503	160	4	400	400	NUM
eurjchem-503	160	5	mhz	mhz	NOUN
eurjchem-503	160	6	,	,	PUNCT
eurjchem-503	160	7	cdcl3	cdcl3	NOUN
eurjchem-503	160	8	,	,	PUNCT
eurjchem-503	160	9			NUM
eurjchem-503	160	10	,	,	PUNCT
eurjchem-503	160	11	ppm	ppm	NUM
eurjchem-503	160	12	):	):	PUNCT
eurjchem-503	160	13	7.65	7.65	NUM
eurjchem-503	160	14	(	(	PUNCT
eurjchem-503	160	15	1h	1h	NUM
eurjchem-503	160	16	,	,	PUNCT
eurjchem-503	160	17	s	s	X
eurjchem-503	160	18	,	,	PUNCT
eurjchem-503	160	19	nh	nh	PROPN
eurjchem-503	160	20	)	)	PUNCT
eurjchem-503	160	21	,	,	PUNCT
eurjchem-503	160	22	7.42	7.42	NUM
eurjchem-503	160	23	(	(	PUNCT
eurjchem-503	160	24	1h	1h	NUM
eurjchem-503	160	25	,	,	PUNCT
eurjchem-503	160	26	d	d	PROPN
eurjchem-503	160	27	,	,	PUNCT
eurjchem-503	160	28	j	j	PROPN
eurjchem-503	160	29	=	=	SYM
eurjchem-503	160	30	8.1	8.1	NUM
eurjchem-503	160	31	hz	hz	NOUN
eurjchem-503	160	32	,	,	PUNCT
eurjchem-503	160	33	9‐h	9‐h	NOUN
eurjchem-503	160	34	)	)	PUNCT
eurjchem-503	160	35	,	,	PUNCT
eurjchem-503	160	36	6.93	6.93	NUM
eurjchem-503	160	37	(	(	PUNCT
eurjchem-503	160	38	1h	1h	NUM
eurjchem-503	160	39	,	,	PUNCT
eurjchem-503	160	40	d	d	PROPN
eurjchem-503	160	41	,	,	PUNCT
eurjchem-503	160	42	j	j	PROPN
eurjchem-503	161	1	=	=	SYM
eurjchem-503	162	1	2.1	2.1	NUM
eurjchem-503	162	2	hz	hz	NOUN
eurjchem-503	162	3	,	,	PUNCT
eurjchem-503	162	4	12‐h	12‐h	NUM
eurjchem-503	162	5	)	)	PUNCT
eurjchem-503	162	6	,	,	PUNCT
eurjchem-503	162	7	6.85	6.85	NUM
eurjchem-503	162	8	(	(	PUNCT
eurjchem-503	162	9	1h	1h	NUM
eurjchem-503	162	10	,	,	PUNCT
eurjchem-503	162	11	dd	dd	NOUN
eurjchem-503	162	12	,	,	PUNCT
eurjchem-503	162	13	j	j	PROPN
eurjchem-503	162	14	=	=	SYM
eurjchem-503	162	15	8.1	8.1	NUM
eurjchem-503	162	16	,	,	PUNCT
eurjchem-503	162	17	2.1	2.1	NUM
eurjchem-503	162	18	hz	hz	NOUN
eurjchem-503	162	19	,	,	PUNCT
eurjchem-503	162	20	10‐h	10‐h	NUM
eurjchem-503	162	21	)	)	PUNCT
eurjchem-503	162	22	,	,	PUNCT
eurjchem-503	162	23	3.80	3.80	NUM
eurjchem-503	162	24	(	(	PUNCT
eurjchem-503	162	25	3h	3h	NUM
eurjchem-503	162	26	,	,	PUNCT
eurjchem-503	162	27	s	s	X
eurjchem-503	162	28	,	,	PUNCT
eurjchem-503	162	29	ome	ome	PROPN
eurjchem-503	162	30	)	)	PUNCT
eurjchem-503	162	31	,	,	PUNCT
eurjchem-503	162	32	3.53	3.53	NUM
eurjchem-503	162	33	(	(	PUNCT
eurjchem-503	162	34	1h	1h	NUM
eurjchem-503	162	35	,	,	PUNCT
eurjchem-503	162	36	brd	brd	PROPN
eurjchem-503	162	37	,	,	PUNCT
eurjchem-503	162	38	j	j	PROPN
eurjchem-503	163	1	=	=	PROPN
eurjchem-503	163	2	12	12	NUM
eurjchem-503	163	3	hz	hz	VERB
eurjchem-503	163	4	,	,	PUNCT
eurjchem-503	163	5	3‐h	3‐h	NUM
eurjchem-503	163	6	)	)	PUNCT
eurjchem-503	163	7	,	,	PUNCT
eurjchem-503	163	8	3.31	3.31	NUM
eurjchem-503	163	9	(	(	PUNCT
eurjchem-503	163	10	1h	1h	NUM
eurjchem-503	163	11	,	,	PUNCT
eurjchem-503	163	12	dd	dd	NOUN
eurjchem-503	163	13	,	,	PUNCT
eurjchem-503	163	14	j	j	PROPN
eurjchem-503	164	1	=	=	SYM
eurjchem-503	164	2	3.2	3.2	NUM
eurjchem-503	164	3	and	and	CCONJ
eurjchem-503	164	4	1.6	1.6	NUM
eurjchem-503	164	5	hz	hz	NOUN
eurjchem-503	164	6	,	,	PUNCT
eurjchem-503	164	7	19‐h	19‐h	NUM
eurjchem-503	164	8	)	)	PUNCT
eurjchem-503	164	9	,	,	PUNCT
eurjchem-503	164	10	3.43	3.43	NUM
eurjchem-503	164	11	(	(	PUNCT
eurjchem-503	164	12	1h	1h	NUM
eurjchem-503	164	13	,	,	PUNCT
eurjchem-503	164	14	dd	dd	NOUN
eurjchem-503	164	15	,	,	PUNCT
eurjchem-503	164	16	j	j	PROPN
eurjchem-503	164	17	=	=	SYM
eurjchem-503	164	18	3.6	3.6	NUM
eurjchem-503	164	19	hz	hz	NOUN
eurjchem-503	164	20	,	,	PUNCT
eurjchem-503	164	21	18‐h	18‐h	NUM
eurjchem-503	164	22	)	)	PUNCT
eurjchem-503	164	23	,	,	PUNCT
eurjchem-503	164	24	2.97‐2.85	2.97‐2.85	NUM
eurjchem-503	164	25	(	(	PUNCT
eurjchem-503	164	26	6h	6h	NUM
eurjchem-503	164	27	,	,	PUNCT
eurjchem-503	164	28	m	m	PROPN
eurjchem-503	164	29	,	,	PUNCT
eurjchem-503	164	30	5‐h2	5‐h2	PROPN
eurjchem-503	164	31	,	,	PUNCT
eurjchem-503	164	32	6‐h2	6‐h2	NUM
eurjchem-503	164	33	and	and	CCONJ
eurjchem-503	164	34	21‐h2	21‐h2	NUM
eurjchem-503	164	35	)	)	PUNCT
eurjchem-503	164	36	,	,	PUNCT
eurjchem-503	164	37	2.81	2.81	NUM
eurjchem-503	164	38	(	(	PUNCT
eurjchem-503	164	39	1h	1h	NUM
eurjchem-503	164	40	,	,	PUNCT
eurjchem-503	164	41	brd	brd	PROPN
eurjchem-503	164	42	,	,	PUNCT
eurjchem-503	164	43	j	j	PROPN
eurjchem-503	165	1	=	=	SYM
eurjchem-503	165	2	13	13	NUM
eurjchem-503	165	3	and	and	CCONJ
eurjchem-503	165	4	3.5	3.5	NUM
eurjchem-503	165	5	hz	hz	NOUN
eurjchem-503	165	6	,	,	PUNCT
eurjchem-503	165	7	16‐h	16‐h	NUM
eurjchem-503	165	8	)	)	PUNCT
eurjchem-503	165	9	,	,	PUNCT
eurjchem-503	165	10	2.66	2.66	NUM
eurjchem-503	165	11	(	(	PUNCT
eurjchem-503	165	12	1h	1h	NUM
eurjchem-503	165	13	,	,	PUNCT
eurjchem-503	165	14	brd	brd	PROPN
eurjchem-503	165	15	,	,	PUNCT
eurjchem-503	165	16	j	j	PROPN
eurjchem-503	166	1	=	=	PROPN
eurjchem-503	166	2	12.9	12.9	NUM
eurjchem-503	166	3	hz	hz	VERB
eurjchem-503	166	4	,	,	PUNCT
eurjchem-503	166	5	14‐	14‐	NUM
eurjchem-503	166	6	heq	heq	NOUN
eurjchem-503	166	7	)	)	PUNCT
eurjchem-503	166	8	,	,	PUNCT
eurjchem-503	166	9	2.65	2.65	NUM
eurjchem-503	166	10	(	(	PUNCT
eurjchem-503	166	11	1h	1h	NUM
eurjchem-503	166	12	,	,	PUNCT
eurjchem-503	166	13	q	q	NOUN
eurjchem-503	166	14	,	,	PUNCT
eurjchem-503	166	15	j	j	PROPN
eurjchem-503	167	1	=	=	PROPN
eurjchem-503	167	2	11.2	11.2	NUM
eurjchem-503	167	3	hz	hz	NOUN
eurjchem-503	167	4	,	,	PUNCT
eurjchem-503	167	5	14‐hax	14‐hax	NUM
eurjchem-503	167	6	)	)	PUNCT
eurjchem-503	167	7	.	.	PUNCT
eurjchem-503	168	1	2.54	2.54	NUM
eurjchem-503	168	2	(	(	PUNCT
eurjchem-503	168	3	1h	1h	NUM
eurjchem-503	168	4	,	,	PUNCT
eurjchem-503	168	5	dd	dd	NOUN
eurjchem-503	168	6	,	,	PUNCT
eurjchem-503	168	7	j	j	PROPN
eurjchem-503	168	8	=	=	SYM
eurjchem-503	168	9	15	15	NUM
eurjchem-503	168	10	hz	hz	NOUN
eurjchem-503	168	11	and	and	CCONJ
eurjchem-503	168	12	5	5	NUM
eurjchem-503	168	13	hz	hz	NOUN
eurjchem-503	168	14	,	,	PUNCT
eurjchem-503	168	15	16‐h	16‐h	NUM
eurjchem-503	168	16	)	)	PUNCT
eurjchem-503	168	17	,	,	PUNCT
eurjchem-503	168	18	2.51	2.51	NUM
eurjchem-503	168	19	(	(	PUNCT
eurjchem-503	168	20	1h	1h	NUM
eurjchem-503	168	21	,	,	PUNCT
eurjchem-503	168	22	brs	br	VERB
eurjchem-503	168	23	,	,	PUNCT
eurjchem-503	168	24	20‐h	20‐h	NUM
eurjchem-503	168	25	)	)	PUNCT
eurjchem-503	168	26	,	,	PUNCT
eurjchem-503	168	27	2.25	2.25	NUM
eurjchem-503	168	28	(	(	PUNCT
eurjchem-503	168	29	1h	1h	NUM
eurjchem-503	168	30	,	,	PUNCT
eurjchem-503	168	31	brd	brd	PROPN
eurjchem-503	168	32	,	,	PUNCT
eurjchem-503	168	33	j	j	PROPN
eurjchem-503	169	1	=	=	PROPN
eurjchem-503	169	2	11.7	11.7	NUM
eurjchem-503	169	3	hz	hz	NOUN
eurjchem-503	169	4	,	,	PUNCT
eurjchem-503	169	5	15‐h	15‐h	NUM
eurjchem-503	169	6	)	)	PUNCT
eurjchem-503	169	7	.	.	PUNCT
eurjchem-503	170	1	ms	ms	NOUN
eurjchem-503	170	2	(	(	PUNCT
eurjchem-503	170	3	m	m	PROPN
eurjchem-503	170	4	/	/	SYM
eurjchem-503	170	5	z	z	NOUN
eurjchem-503	170	6	,	,	PUNCT
eurjchem-503	170	7	ei	ei	PROPN
eurjchem-503	170	8	):	):	PUNCT
eurjchem-503	170	9	338	338	NUM
eurjchem-503	170	10	;	;	PUNCT
eurjchem-503	170	11	hrms	hrm	VERB
eurjchem-503	170	12	calcd	calcd	NOUN
eurjchem-503	170	13	.	.	PUNCT
eurjchem-503	171	1	for	for	ADP
eurjchem-503	171	2	c20h22n2o3	c20h22n2o3	PROPN
eurjchem-503	171	3	(	(	PUNCT
eurjchem-503	171	4	m+	m+	NUM
eurjchem-503	171	5	):	):	PUNCT
eurjchem-503	171	6	338.1630	338.1630	NUM
eurjchem-503	171	7	,	,	PUNCT
eurjchem-503	171	8	found	find	VERB
eurjchem-503	171	9	:	:	PUNCT
eurjchem-503	171	10	338.1625	338.1625	NUM
eurjchem-503	171	11	.	.	NOUN
eurjchem-503	171	12	30	30	NUM
eurjchem-503	171	13	yar	yar	PROPN
eurjchem-503	171	14	et	et	PROPN
eurjchem-503	171	15	al	al	PROPN
eurjchem-503	171	16	.	.	PUNCT
eurjchem-503	171	17	/	/	SYM
eurjchem-503	171	18	european	european	PROPN
eurjchem-503	171	19	journal	journal	PROPN
eurjchem-503	171	20	of	of	ADP
eurjchem-503	171	21	chemistry	chemistry	NOUN
eurjchem-503	171	22	3	3	NUM
eurjchem-503	171	23	(	(	PUNCT
eurjchem-503	171	24	1	1	NUM
eurjchem-503	171	25	)	)	PUNCT
eurjchem-503	171	26	(	(	PUNCT
eurjchem-503	171	27	2012	2012	NUM
eurjchem-503	171	28	)	)	PUNCT
eurjchem-503	171	29	26‐31	26‐31	NUM
eurjchem-503	171	30	2.2.10	2.2.10	NUM
eurjchem-503	171	31	.	.	PUNCT
eurjchem-503	172	1	11,18‐dimethoxy‐	11,18‐dimethoxy‐	NUM
eurjchem-503	173	1	(	(	PUNCT
eurjchem-503	173	2	20α)‐18,19‐didehydro‐yohimban‐	20α)‐18,19‐didehydro‐yohimban‐	NUM
eurjchem-503	173	3	17‐one	17‐one	NUM
eurjchem-503	173	4	(	(	PUNCT
eurjchem-503	173	5	14	14	NUM
eurjchem-503	173	6	)	)	PUNCT
eurjchem-503	173	7	concentrated	concentrated	ADJ
eurjchem-503	173	8	sulfuric	sulfuric	NOUN
eurjchem-503	173	9	acid	acid	NOUN
eurjchem-503	173	10	(	(	PUNCT
eurjchem-503	173	11	0.02	0.02	NUM
eurjchem-503	173	12	ml	ml	NOUN
eurjchem-503	173	13	)	)	PUNCT
eurjchem-503	173	14	was	be	AUX
eurjchem-503	173	15	added	add	VERB
eurjchem-503	173	16	to	to	ADP
eurjchem-503	173	17	a	a	DET
eurjchem-503	173	18	solution	solution	NOUN
eurjchem-503	173	19	of	of	ADP
eurjchem-503	173	20	the	the	DET
eurjchem-503	173	21	epoxy	epoxy	NOUN
eurjchem-503	173	22	ketone	ketone	NOUN
eurjchem-503	173	23	,	,	PUNCT
eurjchem-503	173	24	13	13	NUM
eurjchem-503	173	25	,	,	PUNCT
eurjchem-503	173	26	(	(	PUNCT
eurjchem-503	173	27	30	30	NUM
eurjchem-503	173	28	mg	mg	PROPN
eurjchem-503	173	29	,	,	PUNCT
eurjchem-503	173	30	0.089	0.089	NUM
eurjchem-503	173	31	mmol	mmol	NOUN
eurjchem-503	173	32	)	)	PUNCT
eurjchem-503	173	33	in	in	ADP
eurjchem-503	173	34	methanol	methanol	NOUN
eurjchem-503	173	35	(	(	PUNCT
eurjchem-503	173	36	5	5	NUM
eurjchem-503	173	37	ml	ml	NOUN
eurjchem-503	173	38	)	)	PUNCT
eurjchem-503	173	39	.	.	PUNCT
eurjchem-503	174	1	the	the	DET
eurjchem-503	174	2	resulting	result	VERB
eurjchem-503	174	3	solution	solution	NOUN
eurjchem-503	174	4	was	be	AUX
eurjchem-503	174	5	refluxed	refluxe	VERB
eurjchem-503	174	6	for	for	ADP
eurjchem-503	174	7	6	6	NUM
eurjchem-503	174	8	hours	hour	NOUN
eurjchem-503	174	9	under	under	ADP
eurjchem-503	174	10	argon	argon	NOUN
eurjchem-503	174	11	atmosphere	atmosphere	NOUN
eurjchem-503	174	12	.	.	PUNCT
eurjchem-503	175	1	during	during	ADP
eurjchem-503	175	2	the	the	DET
eurjchem-503	175	3	course	course	NOUN
eurjchem-503	175	4	of	of	ADP
eurjchem-503	175	5	the	the	DET
eurjchem-503	175	6	reaction	reaction	NOUN
eurjchem-503	175	7	,	,	PUNCT
eurjchem-503	175	8	concentrated	concentrated	ADJ
eurjchem-503	175	9	sulfuric	sulfuric	NOUN
eurjchem-503	175	10	acid	acid	NOUN
eurjchem-503	175	11	(	(	PUNCT
eurjchem-503	175	12	0.5	0.5	NUM
eurjchem-503	175	13	ml	ml	NOUN
eurjchem-503	175	14	)	)	PUNCT
eurjchem-503	175	15	was	be	AUX
eurjchem-503	175	16	added	add	VERB
eurjchem-503	175	17	dropwise	dropwise	NOUN
eurjchem-503	175	18	to	to	ADP
eurjchem-503	175	19	the	the	DET
eurjchem-503	175	20	reaction	reaction	NOUN
eurjchem-503	175	21	mixture	mixture	NOUN
eurjchem-503	175	22	.	.	PUNCT
eurjchem-503	176	1	after	after	SCONJ
eurjchem-503	176	2	the	the	DET
eurjchem-503	176	3	temperature	temperature	NOUN
eurjchem-503	176	4	of	of	ADP
eurjchem-503	176	5	the	the	DET
eurjchem-503	176	6	reaction	reaction	NOUN
eurjchem-503	176	7	mixture	mixture	NOUN
eurjchem-503	176	8	reached	reach	VERB
eurjchem-503	176	9	to	to	PART
eurjchem-503	176	10	room	room	NOUN
eurjchem-503	176	11	temperature	temperature	NOUN
eurjchem-503	176	12	,	,	PUNCT
eurjchem-503	176	13	the	the	DET
eurjchem-503	176	14	solution	solution	NOUN
eurjchem-503	176	15	was	be	AUX
eurjchem-503	176	16	made	make	VERB
eurjchem-503	176	17	alkaline	alkaline	NOUN
eurjchem-503	176	18	by	by	ADP
eurjchem-503	176	19	the	the	DET
eurjchem-503	176	20	addition	addition	NOUN
eurjchem-503	176	21	of	of	ADP
eurjchem-503	176	22	sodium	sodium	NOUN
eurjchem-503	176	23	bicarbonate	bicarbonate	NOUN
eurjchem-503	176	24	;	;	PUNCT
eurjchem-503	176	25	the	the	DET
eurjchem-503	176	26	reaction	reaction	NOUN
eurjchem-503	176	27	mixture	mixture	NOUN
eurjchem-503	176	28	was	be	AUX
eurjchem-503	176	29	extracted	extract	VERB
eurjchem-503	176	30	with	with	ADP
eurjchem-503	176	31	methylene	methylene	ADJ
eurjchem-503	176	32	dichloride	dichloride	NOUN
eurjchem-503	176	33	.	.	PUNCT
eurjchem-503	177	1	the	the	DET
eurjchem-503	177	2	extract	extract	NOUN
eurjchem-503	177	3	was	be	AUX
eurjchem-503	177	4	washed	wash	VERB
eurjchem-503	177	5	,	,	PUNCT
eurjchem-503	177	6	dried	dry	VERB
eurjchem-503	177	7	and	and	CCONJ
eurjchem-503	177	8	evaporated	evaporate	VERB
eurjchem-503	177	9	to	to	PART
eurjchem-503	177	10	give	give	VERB
eurjchem-503	177	11	a	a	DET
eurjchem-503	177	12	residue	residue	NOUN
eurjchem-503	177	13	,	,	PUNCT
eurjchem-503	177	14	which	which	PRON
eurjchem-503	177	15	was	be	AUX
eurjchem-503	177	16	further	far	ADV
eurjchem-503	177	17	purified	purify	VERB
eurjchem-503	177	18	by	by	ADP
eurjchem-503	177	19	recrystallization	recrystallization	NOUN
eurjchem-503	177	20	from	from	ADP
eurjchem-503	177	21	methanol	methanol	NOUN
eurjchem-503	177	22	to	to	ADP
eurjchem-503	177	23	afforded	afford	VERB
eurjchem-503	177	24	18‐methoxyenone	18‐methoxyenone	NUM
eurjchem-503	177	25	,	,	PUNCT
eurjchem-503	177	26	14	14	NUM
eurjchem-503	177	27	,	,	PUNCT
eurjchem-503	177	28	as	as	ADP
eurjchem-503	177	29	light	light	ADJ
eurjchem-503	177	30	yellow	yellow	ADJ
eurjchem-503	177	31	crystals	crystal	NOUN
eurjchem-503	177	32	(	(	PUNCT
eurjchem-503	177	33	scheme	scheme	NOUN
eurjchem-503	177	34	3	3	NUM
eurjchem-503	177	35	)	)	PUNCT
eurjchem-503	177	36	.	.	PUNCT
eurjchem-503	178	1	m.p.:149‐153	m.p.:149‐153	VERB
eurjchem-503	178	2	oc	oc	PROPN
eurjchem-503	178	3	.	.	PROPN
eurjchem-503	178	4	yield	yield	NOUN
eurjchem-503	178	5	:	:	PUNCT
eurjchem-503	178	6	27	27	NUM
eurjchem-503	178	7	mg	mg	NOUN
eurjchem-503	178	8	,	,	PUNCT
eurjchem-503	178	9	86	86	NUM
eurjchem-503	178	10	%	%	NOUN
eurjchem-503	178	11	.	.	PUNCT
eurjchem-503	179	1	ir	ir	PROPN
eurjchem-503	179	2	(	(	PUNCT
eurjchem-503	179	3	max	max	PROPN
eurjchem-503	179	4	,	,	PUNCT
eurjchem-503	179	5	thin	thin	ADJ
eurjchem-503	179	6	film	film	NOUN
eurjchem-503	179	7	,	,	PUNCT
eurjchem-503	179	8	cm‐1	cm‐1	PROPN
eurjchem-503	179	9	):	):	PUNCT
eurjchem-503	179	10	3350	3350	NUM
eurjchem-503	179	11	(	(	PUNCT
eurjchem-503	179	12	nh	nh	NOUN
eurjchem-503	179	13	)	)	PUNCT
eurjchem-503	179	14	,	,	PUNCT
eurjchem-503	179	15	1681	1681	NUM
eurjchem-503	179	16	(	(	PUNCT
eurjchem-503	179	17	c	c	NOUN
eurjchem-503	179	18	=	=	NOUN
eurjchem-503	179	19	c‐co	c‐co	NOUN
eurjchem-503	179	20	)	)	PUNCT
eurjchem-503	179	21	,	,	PUNCT
eurjchem-503	179	22	1628	1628	NUM
eurjchem-503	179	23	(	(	PUNCT
eurjchem-503	179	24	c	c	NOUN
eurjchem-503	179	25	=	=	SYM
eurjchem-503	179	26	c	c	NOUN
eurjchem-503	179	27	)	)	PUNCT
eurjchem-503	179	28	.	.	PUNCT
eurjchem-503	180	1	1h	1h	NUM
eurjchem-503	180	2	nmr	nmr	NOUN
eurjchem-503	180	3	(	(	PUNCT
eurjchem-503	180	4	400	400	NUM
eurjchem-503	180	5	mhz	mhz	NOUN
eurjchem-503	180	6	,	,	PUNCT
eurjchem-503	180	7	cdcl3	cdcl3	NOUN
eurjchem-503	180	8	,	,	PUNCT
eurjchem-503	180	9			NUM
eurjchem-503	180	10	,	,	PUNCT
eurjchem-503	180	11	ppm	ppm	NUM
eurjchem-503	180	12	):	):	PUNCT
eurjchem-503	180	13	7.76	7.76	NUM
eurjchem-503	180	14	(	(	PUNCT
eurjchem-503	180	15	1h	1h	NUM
eurjchem-503	180	16	,	,	PUNCT
eurjchem-503	180	17	s	s	X
eurjchem-503	180	18	,	,	PUNCT
eurjchem-503	180	19	nh	nh	PROPN
eurjchem-503	180	20	)	)	PUNCT
eurjchem-503	180	21	,	,	PUNCT
eurjchem-503	180	22	7.46	7.46	NUM
eurjchem-503	180	23	(	(	PUNCT
eurjchem-503	180	24	1h	1h	NUM
eurjchem-503	180	25	,	,	PUNCT
eurjchem-503	180	26	d	d	PROPN
eurjchem-503	180	27	,	,	PUNCT
eurjchem-503	180	28	j	j	PROPN
eurjchem-503	180	29	=	=	PROPN
eurjchem-503	180	30	8.2	8.2	NUM
eurjchem-503	180	31	hz	hz	ADJ
eurjchem-503	180	32	,	,	PUNCT
eurjchem-503	180	33	9‐h	9‐h	NOUN
eurjchem-503	180	34	)	)	PUNCT
eurjchem-503	180	35	,	,	PUNCT
eurjchem-503	180	36	6.91	6.91	NUM
eurjchem-503	180	37	(	(	PUNCT
eurjchem-503	180	38	1h	1h	NUM
eurjchem-503	180	39	,	,	PUNCT
eurjchem-503	180	40	d	d	PROPN
eurjchem-503	180	41	,	,	PUNCT
eurjchem-503	180	42	j	j	PROPN
eurjchem-503	181	1	=	=	SYM
eurjchem-503	181	2	2.0	2.0	NUM
eurjchem-503	181	3	hz	hz	NOUN
eurjchem-503	181	4	,	,	PUNCT
eurjchem-503	181	5	12‐h	12‐h	NUM
eurjchem-503	181	6	)	)	PUNCT
eurjchem-503	181	7	,	,	PUNCT
eurjchem-503	181	8	6.81	6.81	NUM
eurjchem-503	181	9	(	(	PUNCT
eurjchem-503	181	10	1h	1h	NUM
eurjchem-503	181	11	,	,	PUNCT
eurjchem-503	181	12	dd	dd	NOUN
eurjchem-503	181	13	,	,	PUNCT
eurjchem-503	181	14	j	j	PROPN
eurjchem-503	182	1	=	=	SYM
eurjchem-503	182	2	8.2	8.2	NUM
eurjchem-503	182	3	and	and	CCONJ
eurjchem-503	182	4	2.0	2.0	NUM
eurjchem-503	182	5	hz	hz	NOUN
eurjchem-503	182	6	,	,	PUNCT
eurjchem-503	182	7	10‐h	10‐h	NUM
eurjchem-503	182	8	)	)	PUNCT
eurjchem-503	182	9	,	,	PUNCT
eurjchem-503	182	10	5.34	5.34	NUM
eurjchem-503	182	11	(	(	PUNCT
eurjchem-503	182	12	1h	1h	NUM
eurjchem-503	182	13	,	,	PUNCT
eurjchem-503	182	14	brs	br	VERB
eurjchem-503	182	15	,	,	PUNCT
eurjchem-503	182	16	19‐h	19‐h	NUM
eurjchem-503	182	17	)	)	PUNCT
eurjchem-503	182	18	,	,	PUNCT
eurjchem-503	182	19	3.80	3.80	NUM
eurjchem-503	182	20	(	(	PUNCT
eurjchem-503	182	21	3h	3h	NUM
eurjchem-503	182	22	,	,	PUNCT
eurjchem-503	182	23	s	s	X
eurjchem-503	182	24	,	,	PUNCT
eurjchem-503	182	25	ome	ome	PROPN
eurjchem-503	182	26	)	)	PUNCT
eurjchem-503	182	27	,	,	PUNCT
eurjchem-503	182	28	3.66	3.66	NUM
eurjchem-503	182	29	(	(	PUNCT
eurjchem-503	182	30	3h	3h	NUM
eurjchem-503	182	31	,	,	PUNCT
eurjchem-503	182	32	s	s	X
eurjchem-503	182	33	,	,	PUNCT
eurjchem-503	182	34	ome	ome	PROPN
eurjchem-503	182	35	)	)	PUNCT
eurjchem-503	182	36	,	,	PUNCT
eurjchem-503	182	37	3.34	3.34	NUM
eurjchem-503	182	38	(	(	PUNCT
eurjchem-503	182	39	1h	1h	NUM
eurjchem-503	182	40	,	,	PUNCT
eurjchem-503	182	41	brd	brd	PROPN
eurjchem-503	182	42	,	,	PUNCT
eurjchem-503	182	43	j	j	PROPN
eurjchem-503	182	44	=	=	PROPN
eurjchem-503	182	45	12	12	NUM
eurjchem-503	182	46	hz	hz	VERB
eurjchem-503	182	47	,	,	PUNCT
eurjchem-503	182	48	3‐h	3‐h	NUM
eurjchem-503	182	49	)	)	PUNCT
eurjchem-503	182	50	,	,	PUNCT
eurjchem-503	182	51	3.12‐3.01	3.12‐3.01	NUM
eurjchem-503	182	52	(	(	PUNCT
eurjchem-503	182	53	2h	2h	NUM
eurjchem-503	182	54	,	,	PUNCT
eurjchem-503	182	55	m	m	PROPN
eurjchem-503	182	56	,	,	PUNCT
eurjchem-503	182	57	21‐h2	21‐h2	PROPN
eurjchem-503	182	58	)	)	PUNCT
eurjchem-503	182	59	,	,	PUNCT
eurjchem-503	182	60	2.73	2.73	NUM
eurjchem-503	182	61	(	(	PUNCT
eurjchem-503	182	62	1h	1h	NUM
eurjchem-503	182	63	,	,	PUNCT
eurjchem-503	182	64	brs	br	VERB
eurjchem-503	182	65	,	,	PUNCT
eurjchem-503	182	66	20‐h	20‐h	NUM
eurjchem-503	182	67	)	)	PUNCT
eurjchem-503	182	68	,	,	PUNCT
eurjchem-503	182	69	2.59‐2.49	2.59‐2.49	NUM
eurjchem-503	182	70	(	(	PUNCT
eurjchem-503	182	71	2h	2h	NUM
eurjchem-503	182	72	,	,	PUNCT
eurjchem-503	182	73	m	m	PROPN
eurjchem-503	182	74	16‐h2	16‐h2	PROPN
eurjchem-503	182	75	)	)	PUNCT
eurjchem-503	182	76	,	,	PUNCT
eurjchem-503	182	77	2.43‐2.35	2.43‐2.35	NUM
eurjchem-503	182	78	(	(	PUNCT
eurjchem-503	182	79	4h	4h	NUM
eurjchem-503	182	80	,	,	PUNCT
eurjchem-503	182	81	m	m	PROPN
eurjchem-503	182	82	,	,	PUNCT
eurjchem-503	182	83	6‐h2	6‐h2	NUM
eurjchem-503	182	84	,	,	PUNCT
eurjchem-503	182	85	and	and	CCONJ
eurjchem-503	182	86	5‐h2),2.30	5‐h2),2.30	NUM
eurjchem-503	182	87	(	(	PUNCT
eurjchem-503	182	88	1h	1h	NUM
eurjchem-503	182	89	,	,	PUNCT
eurjchem-503	182	90	dt	dt	PROPN
eurjchem-503	182	91	,	,	PUNCT
eurjchem-503	182	92	j	j	PROPN
eurjchem-503	182	93	=	=	PROPN
eurjchem-503	182	94	11.5	11.5	NUM
eurjchem-503	182	95	and	and	CCONJ
eurjchem-503	182	96	2.9	2.9	NUM
eurjchem-503	182	97	hz	hz	NOUN
eurjchem-503	182	98	,	,	PUNCT
eurjchem-503	182	99	14‐heq	14‐heq	NUM
eurjchem-503	182	100	)	)	PUNCT
eurjchem-503	182	101	,	,	PUNCT
eurjchem-503	182	102	2.27‐	2.27‐	NUM
eurjchem-503	182	103	2.18	2.18	NUM
eurjchem-503	182	104	(	(	PUNCT
eurjchem-503	182	105	5h	5h	NUM
eurjchem-503	182	106	,	,	PUNCT
eurjchem-503	182	107	m	m	PROPN
eurjchem-503	182	108	,	,	PUNCT
eurjchem-503	182	109	6‐h2	6‐h2	NUM
eurjchem-503	182	110	,	,	PUNCT
eurjchem-503	182	111	and	and	CCONJ
eurjchem-503	182	112	5‐h2	5‐h2	NUM
eurjchem-503	182	113	,	,	PUNCT
eurjchem-503	182	114	15‐h	15‐h	NUM
eurjchem-503	182	115	)	)	PUNCT
eurjchem-503	182	116	,	,	PUNCT
eurjchem-503	182	117	2.07	2.07	NUM
eurjchem-503	182	118	(	(	PUNCT
eurjchem-503	182	119	1h	1h	NUM
eurjchem-503	182	120	,	,	PUNCT
eurjchem-503	182	121	q	q	NOUN
eurjchem-503	182	122	,	,	PUNCT
eurjchem-503	182	123	11.6	11.6	NUM
eurjchem-503	182	124	hz	hz	NOUN
eurjchem-503	182	125	,	,	PUNCT
eurjchem-503	182	126	14‐h	14‐h	NUM
eurjchem-503	182	127	ax	ax	NOUN
eurjchem-503	182	128	)	)	PUNCT
eurjchem-503	182	129	.	.	PUNCT
eurjchem-503	183	1	ms	ms	NOUN
eurjchem-503	183	2	(	(	PUNCT
eurjchem-503	183	3	m	m	PROPN
eurjchem-503	183	4	/	/	SYM
eurjchem-503	183	5	z	z	NOUN
eurjchem-503	183	6	,	,	PUNCT
eurjchem-503	183	7	ei	ei	PROPN
eurjchem-503	183	8	):	):	PUNCT
eurjchem-503	183	9	352	352	NUM
eurjchem-503	183	10	;	;	PUNCT
eurjchem-503	183	11	hrms	hrm	VERB
eurjchem-503	183	12	calcd	calcd	NOUN
eurjchem-503	183	13	.	.	PUNCT
eurjchem-503	184	1	for	for	ADP
eurjchem-503	184	2	c20h22n2o3	c20h22n2o3	PROPN
eurjchem-503	184	3	(	(	PUNCT
eurjchem-503	184	4	m+	m+	NUM
eurjchem-503	184	5	):	):	PUNCT
eurjchem-503	184	6	352.1787	352.1787	NUM
eurjchem-503	184	7	,	,	PUNCT
eurjchem-503	184	8	found	find	VERB
eurjchem-503	184	9	:	:	PUNCT
eurjchem-503	184	10	352.1782	352.1782	NUM
eurjchem-503	184	11	.	.	NOUN
eurjchem-503	184	12	3	3	NUM
eurjchem-503	184	13	.	.	NOUN
eurjchem-503	184	14	results	result	NOUN
eurjchem-503	184	15	and	and	CCONJ
eurjchem-503	184	16	discussion	discussion	NOUN
eurjchem-503	184	17	we	we	PRON
eurjchem-503	184	18	began	begin	VERB
eurjchem-503	184	19	our	our	PRON
eurjchem-503	184	20	studies	study	NOUN
eurjchem-503	184	21	with	with	ADP
eurjchem-503	184	22	the	the	DET
eurjchem-503	184	23	photocyclization	photocyclization	NOUN
eurjchem-503	184	24	of	of	ADP
eurjchem-503	184	25	enamide	enamide	NOUN
eurjchem-503	184	26	4	4	NUM
eurjchem-503	184	27	,	,	PUNCT
eurjchem-503	184	28	elected	elect	VERB
eurjchem-503	184	29	as	as	ADP
eurjchem-503	184	30	a	a	DET
eurjchem-503	184	31	model	model	NOUN
eurjchem-503	184	32	substrate	substrate	NOUN
eurjchem-503	184	33	(	(	PUNCT
eurjchem-503	184	34	scheme	scheme	NOUN
eurjchem-503	184	35	1	1	NUM
eurjchem-503	184	36	)	)	PUNCT
eurjchem-503	184	37	,	,	PUNCT
eurjchem-503	184	38	which	which	PRON
eurjchem-503	184	39	was	be	AUX
eurjchem-503	184	40	synthesized	synthesize	VERB
eurjchem-503	184	41	in	in	ADP
eurjchem-503	184	42	high	high	ADJ
eurjchem-503	184	43	yield	yield	NOUN
eurjchem-503	184	44	from	from	ADP
eurjchem-503	184	45	harmaline	harmaline	NOUN
eurjchem-503	184	46	,	,	PUNCT
eurjchem-503	184	47	2	2	NUM
eurjchem-503	184	48	,	,	PUNCT
eurjchem-503	184	49	and	and	CCONJ
eurjchem-503	184	50	benzoyl	benzoyl	ADJ
eurjchem-503	184	51	chloride	chloride	NOUN
eurjchem-503	184	52	,	,	PUNCT
eurjchem-503	184	53	3	3	NUM
eurjchem-503	184	54	,	,	PUNCT
eurjchem-503	184	55	in	in	ADP
eurjchem-503	184	56	the	the	DET
eurjchem-503	184	57	presence	presence	NOUN
eurjchem-503	184	58	of	of	ADP
eurjchem-503	184	59	triethylamine	triethylamine	NOUN
eurjchem-503	184	60	.	.	PUNCT
eurjchem-503	185	1	a	a	DET
eurjchem-503	185	2	number	number	NOUN
eurjchem-503	185	3	of	of	ADP
eurjchem-503	185	4	photocyclization	photocyclization	NOUN
eurjchem-503	185	5	reaction	reaction	NOUN
eurjchem-503	185	6	conditions	condition	NOUN
eurjchem-503	185	7	were	be	AUX
eurjchem-503	185	8	optimized	optimize	VERB
eurjchem-503	185	9	,	,	PUNCT
eurjchem-503	185	10	and	and	CCONJ
eurjchem-503	185	11	it	it	PRON
eurjchem-503	185	12	was	be	AUX
eurjchem-503	185	13	observed	observe	VERB
eurjchem-503	185	14	that	that	SCONJ
eurjchem-503	185	15	in	in	ADP
eurjchem-503	185	16	photocyclization	photocyclization	NOUN
eurjchem-503	185	17	step	step	NOUN
eurjchem-503	185	18	,	,	PUNCT
eurjchem-503	185	19	the	the	DET
eurjchem-503	185	20	duration	duration	NOUN
eurjchem-503	185	21	of	of	ADP
eurjchem-503	185	22	irradiation	irradiation	NOUN
eurjchem-503	185	23	is	be	AUX
eurjchem-503	185	24	extremely	extremely	ADV
eurjchem-503	185	25	important	important	ADJ
eurjchem-503	185	26	.	.	PUNCT
eurjchem-503	186	1	initially	initially	ADV
eurjchem-503	186	2	,	,	PUNCT
eurjchem-503	186	3	irradiation	irradiation	NOUN
eurjchem-503	186	4	of	of	ADP
eurjchem-503	186	5	enamide	enamide	NOUN
eurjchem-503	186	6	,	,	PUNCT
eurjchem-503	186	7	4	4	NUM
eurjchem-503	186	8	,	,	PUNCT
eurjchem-503	186	9	using	use	VERB
eurjchem-503	186	10	high	high	ADJ
eurjchem-503	186	11	pressure	pressure	NOUN
eurjchem-503	186	12	mercury	mercury	NOUN
eurjchem-503	186	13	lamp	lamp	NOUN
eurjchem-503	186	14	at	at	ADP
eurjchem-503	186	15	0‐5	0‐5	NUM
eurjchem-503	186	16	oc	oc	NOUN
eurjchem-503	186	17	for	for	ADP
eurjchem-503	186	18	6	6	NUM
eurjchem-503	186	19	hours	hour	NOUN
eurjchem-503	186	20	in	in	ADP
eurjchem-503	186	21	the	the	DET
eurjchem-503	186	22	presence	presence	NOUN
eurjchem-503	186	23	of	of	ADP
eurjchem-503	186	24	sodium	sodium	NOUN
eurjchem-503	186	25	borohydride	borohydride	NOUN
eurjchem-503	186	26	and	and	CCONJ
eurjchem-503	186	27	acetonitrile	acetonitrile	NOUN
eurjchem-503	186	28	:	:	PUNCT
eurjchem-503	186	29	methanol	methanol	NOUN
eurjchem-503	186	30	(	(	PUNCT
eurjchem-503	186	31	9:1	9:1	NUM
eurjchem-503	186	32	)	)	PUNCT
eurjchem-503	186	33	afforded	afford	VERB
eurjchem-503	186	34	only	only	ADV
eurjchem-503	186	35	the	the	DET
eurjchem-503	186	36	undesired	undesired	ADJ
eurjchem-503	186	37	lactam	lactam	NOUN
eurjchem-503	186	38	,	,	PUNCT
eurjchem-503	186	39	5	5	NUM
eurjchem-503	186	40	,	,	PUNCT
eurjchem-503	186	41	in	in	ADP
eurjchem-503	186	42	92	92	NUM
eurjchem-503	186	43	%	%	NOUN
eurjchem-503	186	44	yield	yield	NOUN
eurjchem-503	186	45	.	.	PUNCT
eurjchem-503	187	1	however	however	ADV
eurjchem-503	187	2	,	,	PUNCT
eurjchem-503	187	3	to	to	ADP
eurjchem-503	187	4	our	our	PRON
eurjchem-503	187	5	delight	delight	NOUN
eurjchem-503	187	6	enamide	enamide	ADV
eurjchem-503	187	7	,	,	PUNCT
eurjchem-503	187	8	4	4	NUM
eurjchem-503	187	9	,	,	PUNCT
eurjchem-503	187	10	produced	produce	VERB
eurjchem-503	187	11	the	the	DET
eurjchem-503	187	12	required	require	VERB
eurjchem-503	187	13	lactam	lactam	NOUN
eurjchem-503	187	14	,	,	PUNCT
eurjchem-503	187	15	6	6	NUM
eurjchem-503	187	16	,	,	PUNCT
eurjchem-503	187	17	in	in	ADP
eurjchem-503	187	18	good	good	ADJ
eurjchem-503	187	19	yield	yield	NOUN
eurjchem-503	187	20	under	under	ADP
eurjchem-503	187	21	the	the	DET
eurjchem-503	187	22	same	same	ADJ
eurjchem-503	187	23	reaction	reaction	NOUN
eurjchem-503	187	24	condition	condition	NOUN
eurjchem-503	187	25	as	as	SCONJ
eurjchem-503	187	26	described	describe	VERB
eurjchem-503	187	27	above	above	ADV
eurjchem-503	187	28	except	except	SCONJ
eurjchem-503	187	29	when	when	SCONJ
eurjchem-503	187	30	the	the	DET
eurjchem-503	187	31	6	6	NUM
eurjchem-503	187	32	hours	hour	NOUN
eurjchem-503	187	33	irradiation	irradiation	NOUN
eurjchem-503	187	34	was	be	AUX
eurjchem-503	187	35	replaced	replace	VERB
eurjchem-503	187	36	by	by	ADP
eurjchem-503	187	37	1	1	NUM
eurjchem-503	187	38	hour	hour	NOUN
eurjchem-503	187	39	irradiation	irradiation	NOUN
eurjchem-503	187	40	.	.	PUNCT
eurjchem-503	188	1	however	however	ADV
eurjchem-503	188	2	it	it	PRON
eurjchem-503	188	3	was	be	AUX
eurjchem-503	188	4	observed	observe	VERB
eurjchem-503	188	5	that	that	SCONJ
eurjchem-503	188	6	starting	starting	NOUN
eurjchem-503	188	7	material	material	NOUN
eurjchem-503	188	8	was	be	AUX
eurjchem-503	188	9	disappeared	disappear	VERB
eurjchem-503	188	10	in	in	ADP
eurjchem-503	188	11	1	1	NUM
eurjchem-503	188	12	hour	hour	NOUN
eurjchem-503	188	13	time	time	NOUN
eurjchem-503	188	14	during	during	ADP
eurjchem-503	188	15	the	the	DET
eurjchem-503	188	16	formation	formation	NOUN
eurjchem-503	188	17	of	of	ADP
eurjchem-503	188	18	5	5	NUM
eurjchem-503	188	19	or	or	CCONJ
eurjchem-503	188	20	6	6	NUM
eurjchem-503	188	21	.	.	NOUN
eurjchem-503	188	22	3.1	3.1	NUM
eurjchem-503	188	23	.	.	PUNCT
eurjchem-503	189	1	synthesis	synthesis	NOUN
eurjchem-503	189	2	of	of	ADP
eurjchem-503	189	3	lactam	lactam	NOUN
eurjchem-503	189	4	,	,	PUNCT
eurjchem-503	189	5	9	9	NUM
eurjchem-503	189	6	to	to	PART
eurjchem-503	189	7	target	target	VERB
eurjchem-503	189	8	the	the	DET
eurjchem-503	189	9	required	require	VERB
eurjchem-503	189	10	lactam	lactam	NOUN
eurjchem-503	189	11	9	9	NUM
eurjchem-503	189	12	,	,	PUNCT
eurjchem-503	189	13	harmaline	harmaline	NOUN
eurjchem-503	189	14	,	,	PUNCT
eurjchem-503	189	15	2	2	NUM
eurjchem-503	189	16	,	,	PUNCT
eurjchem-503	189	17	was	be	AUX
eurjchem-503	189	18	treated	treat	VERB
eurjchem-503	189	19	with	with	ADP
eurjchem-503	189	20	p‐anisoyl	p‐anisoyl	PROPN
eurjchem-503	189	21	chloride	chloride	NOUN
eurjchem-503	189	22	,	,	PUNCT
eurjchem-503	189	23	7	7	NUM
eurjchem-503	189	24	,	,	PUNCT
eurjchem-503	189	25	in	in	ADP
eurjchem-503	189	26	the	the	DET
eurjchem-503	189	27	presence	presence	NOUN
eurjchem-503	189	28	of	of	ADP
eurjchem-503	189	29	triethylamine	triethylamine	NOUN
eurjchem-503	189	30	and	and	CCONJ
eurjchem-503	189	31	benzene	benzene	NOUN
eurjchem-503	189	32	,	,	PUNCT
eurjchem-503	189	33	this	this	PRON
eurjchem-503	189	34	produced	produce	VERB
eurjchem-503	189	35	the	the	DET
eurjchem-503	189	36	expected	expect	VERB
eurjchem-503	189	37	enamide	enamide	NOUN
eurjchem-503	189	38	,	,	PUNCT
eurjchem-503	189	39	8	8	NUM
eurjchem-503	189	40	,	,	PUNCT
eurjchem-503	189	41	in	in	ADP
eurjchem-503	189	42	good	good	ADJ
eurjchem-503	189	43	yield	yield	NOUN
eurjchem-503	189	44	(	(	PUNCT
eurjchem-503	189	45	98	98	NUM
eurjchem-503	189	46	%	%	NOUN
eurjchem-503	189	47	)	)	PUNCT
eurjchem-503	189	48	.	.	PUNCT
eurjchem-503	190	1	then	then	ADV
eurjchem-503	190	2	following	follow	VERB
eurjchem-503	190	3	our	our	PRON
eurjchem-503	190	4	previous	previous	ADJ
eurjchem-503	190	5	photocyclization	photocyclization	NOUN
eurjchem-503	190	6	conditions	condition	NOUN
eurjchem-503	190	7	optimized	optimize	VERB
eurjchem-503	190	8	on	on	ADP
eurjchem-503	190	9	model	model	NOUN
eurjchem-503	190	10	enamide	enamide	NOUN
eurjchem-503	190	11	,	,	PUNCT
eurjchem-503	190	12	4	4	NUM
eurjchem-503	190	13	,	,	PUNCT
eurjchem-503	190	14	afforded	afford	VERB
eurjchem-503	190	15	the	the	DET
eurjchem-503	190	16	required	require	VERB
eurjchem-503	190	17	lactam	lactam	NOUN
eurjchem-503	190	18	,	,	PUNCT
eurjchem-503	190	19	9	9	NUM
eurjchem-503	190	20	,	,	PUNCT
eurjchem-503	190	21	in	in	ADP
eurjchem-503	190	22	good	good	ADJ
eurjchem-503	190	23	yield	yield	NOUN
eurjchem-503	190	24	(	(	PUNCT
eurjchem-503	190	25	98	98	NUM
eurjchem-503	190	26	%	%	NOUN
eurjchem-503	190	27	)	)	PUNCT
eurjchem-503	190	28	(	(	PUNCT
eurjchem-503	190	29	scheme	scheme	NOUN
eurjchem-503	190	30	2	2	NUM
eurjchem-503	190	31	)	)	PUNCT
eurjchem-503	190	32	.	.	PUNCT
eurjchem-503	191	1	3.2	3.2	NUM
eurjchem-503	191	2	.	.	PUNCT
eurjchem-503	191	3	transformation	transformation	NOUN
eurjchem-503	191	4	of	of	ADP
eurjchem-503	191	5	lactam	lactam	NOUN
eurjchem-503	191	6	,	,	PUNCT
eurjchem-503	191	7	9	9	NUM
eurjchem-503	191	8	,	,	PUNCT
eurjchem-503	191	9	to	to	PART
eurjchem-503	191	10	advanced	advanced	ADJ
eurjchem-503	191	11	intermediate	intermediate	ADJ
eurjchem-503	191	12	14	14	NUM
eurjchem-503	191	13	then	then	ADV
eurjchem-503	191	14	lactam	lactam	NOUN
eurjchem-503	191	15	,	,	PUNCT
eurjchem-503	191	16	9	9	NUM
eurjchem-503	191	17	,	,	PUNCT
eurjchem-503	191	18	was	be	AUX
eurjchem-503	191	19	reduced	reduce	VERB
eurjchem-503	191	20	with	with	ADP
eurjchem-503	191	21	lithium	lithium	NOUN
eurjchem-503	191	22	aluminum	aluminum	NOUN
eurjchem-503	191	23	hydride	hydride	NOUN
eurjchem-503	191	24	in	in	ADP
eurjchem-503	191	25	diethyl	diethyl	NOUN
eurjchem-503	191	26	ether	ether	NOUN
eurjchem-503	191	27	upon	upon	SCONJ
eurjchem-503	191	28	refluxing	refluxe	VERB
eurjchem-503	191	29	for	for	ADP
eurjchem-503	191	30	2	2	NUM
eurjchem-503	191	31	hours	hour	NOUN
eurjchem-503	191	32	under	under	ADP
eurjchem-503	191	33	the	the	DET
eurjchem-503	191	34	argon	argon	NOUN
eurjchem-503	191	35	atmosphere	atmosphere	NOUN
eurjchem-503	191	36	to	to	PART
eurjchem-503	191	37	give	give	VERB
eurjchem-503	191	38	the	the	DET
eurjchem-503	191	39	corresponding	correspond	VERB
eurjchem-503	191	40	amine	amine	NOUN
eurjchem-503	191	41	,	,	PUNCT
eurjchem-503	191	42	10	10	NUM
eurjchem-503	191	43	,	,	PUNCT
eurjchem-503	191	44	(	(	PUNCT
eurjchem-503	191	45	scheme	scheme	NOUN
eurjchem-503	191	46	3	3	NUM
eurjchem-503	191	47	)	)	PUNCT
eurjchem-503	191	48	.	.	PUNCT
eurjchem-503	192	1	the	the	DET
eurjchem-503	192	2	amine	amine	NOUN
eurjchem-503	192	3	,	,	PUNCT
eurjchem-503	192	4	10	10	NUM
eurjchem-503	192	5	,	,	PUNCT
eurjchem-503	192	6	bearing	bear	VERB
eurjchem-503	192	7	enol‐ether	enol‐ether	ADJ
eurjchem-503	192	8	functionality	functionality	NOUN
eurjchem-503	192	9	in	in	ADP
eurjchem-503	192	10	the	the	DET
eurjchem-503	192	11	ring	ring	NOUN
eurjchem-503	192	12	e	e	NOUN
eurjchem-503	192	13	,	,	PUNCT
eurjchem-503	192	14	was	be	AUX
eurjchem-503	192	15	treated	treat	VERB
eurjchem-503	192	16	with	with	ADP
eurjchem-503	192	17	10	10	NUM
eurjchem-503	192	18	%	%	NOUN
eurjchem-503	192	19	hydrochloric	hydrochloric	ADJ
eurjchem-503	192	20	acid	acid	NOUN
eurjchem-503	192	21	at	at	ADP
eurjchem-503	192	22	room	room	NOUN
eurjchem-503	192	23	temperature	temperature	NOUN
eurjchem-503	192	24	for	for	ADP
eurjchem-503	192	25	one	one	NUM
eurjchem-503	192	26	hour	hour	NOUN
eurjchem-503	192	27	to	to	PART
eurjchem-503	192	28	produce	produce	VERB
eurjchem-503	192	29	the	the	DET
eurjchem-503	192	30	corresponding	corresponding	ADJ
eurjchem-503	192	31	α	α	NOUN
eurjchem-503	192	32	,	,	PUNCT
eurjchem-503	192	33	β‐	β‐	ADJ
eurjchem-503	192	34	unsaturated	unsaturated	ADJ
eurjchem-503	192	35	ketone	ketone	NOUN
eurjchem-503	192	36	,	,	PUNCT
eurjchem-503	192	37	11	11	NUM
eurjchem-503	192	38	.	.	PUNCT
eurjchem-503	193	1	the	the	DET
eurjchem-503	193	2	compound	compound	NOUN
eurjchem-503	193	3	11	11	NUM
eurjchem-503	193	4	exhibited	exhibit	VERB
eurjchem-503	193	5	ir	ir	PROPN
eurjchem-503	193	6	spectrum	spectrum	PROPN
eurjchem-503	193	7	absorption	absorption	NOUN
eurjchem-503	193	8	band	band	NOUN
eurjchem-503	193	9	at	at	ADP
eurjchem-503	193	10	1712	1712	NUM
eurjchem-503	193	11	cm‐1	cm‐1	NOUN
eurjchem-503	193	12	due	due	ADP
eurjchem-503	193	13	to	to	ADP
eurjchem-503	193	14	the	the	DET
eurjchem-503	193	15	presence	presence	NOUN
eurjchem-503	193	16	of	of	ADP
eurjchem-503	193	17	un‐conjugated	un‐conjugated	ADJ
eurjchem-503	193	18	ketone	ketone	NOUN
eurjchem-503	193	19	,	,	PUNCT
eurjchem-503	193	20	and	and	CCONJ
eurjchem-503	193	21	1h‐nmr	1h‐nmr	NUM
eurjchem-503	193	22	signal	signal	NOUN
eurjchem-503	193	23	at	at	ADP
eurjchem-503	193	24			NUM
eurjchem-503	193	25	5.71	5.71	NUM
eurjchem-503	193	26	ppm	ppm	NOUN
eurjchem-503	193	27	(	(	PUNCT
eurjchem-503	193	28	s‐like	s‐like	ADP
eurjchem-503	193	29	,	,	PUNCT
eurjchem-503	193	30	19‐h	19‐h	NUM
eurjchem-503	193	31	)	)	PUNCT
eurjchem-503	193	32	of	of	ADP
eurjchem-503	193	33	olefinic	olefinic	ADJ
eurjchem-503	193	34	proton	proton	NOUN
eurjchem-503	193	35	.	.	PUNCT
eurjchem-503	194	1	the	the	DET
eurjchem-503	194	2	nonconjugated	nonconjugated	ADJ
eurjchem-503	194	3	enone	enone	NOUN
eurjchem-503	194	4	,	,	PUNCT
eurjchem-503	194	5	11	11	NUM
eurjchem-503	194	6	,	,	PUNCT
eurjchem-503	194	7	was	be	AUX
eurjchem-503	194	8	treated	treat	VERB
eurjchem-503	194	9	with	with	ADP
eurjchem-503	194	10	sodium	sodium	NOUN
eurjchem-503	194	11	hydroxide	hydroxide	NOUN
eurjchem-503	194	12	in	in	ADP
eurjchem-503	194	13	methanol	methanol	NOUN
eurjchem-503	194	14	:	:	PUNCT
eurjchem-503	194	15	methylene	methylene	NOUN
eurjchem-503	194	16	dichloride	dichloride	NOUN
eurjchem-503	194	17	(	(	PUNCT
eurjchem-503	194	18	4:1	4:1	NUM
eurjchem-503	194	19	)	)	PUNCT
eurjchem-503	194	20	at	at	ADP
eurjchem-503	194	21	0‐5	0‐5	NUM
eurjchem-503	194	22	oc	oc	NOUN
eurjchem-503	194	23	for	for	ADP
eurjchem-503	194	24	one	one	NUM
eurjchem-503	194	25	and	and	CCONJ
eurjchem-503	194	26	half	half	ADJ
eurjchem-503	194	27	hour	hour	NOUN
eurjchem-503	194	28	to	to	PART
eurjchem-503	194	29	isomerize	isomerize	VERB
eurjchem-503	194	30	the	the	DET
eurjchem-503	194	31	double	double	ADJ
eurjchem-503	194	32	bond	bond	NOUN
eurjchem-503	194	33	to	to	ADP
eurjchem-503	194	34	the	the	DET
eurjchem-503	194	35	conjugated	conjugated	ADJ
eurjchem-503	194	36	position	position	NOUN
eurjchem-503	194	37	to	to	PART
eurjchem-503	194	38	obtain	obtain	VERB
eurjchem-503	194	39	the	the	DET
eurjchem-503	194	40	conjugated	conjugate	VERB
eurjchem-503	194	41	enone	enone	NOUN
eurjchem-503	194	42	,	,	PUNCT
eurjchem-503	194	43	12	12	NUM
eurjchem-503	194	44	.	.	PUNCT
eurjchem-503	195	1	the	the	DET
eurjchem-503	195	2	ir	ir	PROPN
eurjchem-503	195	3	absorption	absorption	NOUN
eurjchem-503	195	4	at	at	ADP
eurjchem-503	195	5	1662	1662	NUM
eurjchem-503	195	6	cm‐1	cm‐1	PROPN
eurjchem-503	195	7	(	(	PUNCT
eurjchem-503	195	8	conjugated	conjugate	VERB
eurjchem-503	195	9	c	c	PROPN
eurjchem-503	195	10	=	=	NOUN
eurjchem-503	195	11	o	o	NOUN
eurjchem-503	195	12	)	)	PUNCT
eurjchem-503	195	13	,	,	PUNCT
eurjchem-503	195	14	and	and	CCONJ
eurjchem-503	195	15	1h	1h	NUM
eurjchem-503	195	16	nmr	nmr	NOUN
eurjchem-503	195	17	signals	signal	NOUN
eurjchem-503	195	18	of	of	ADP
eurjchem-503	195	19	two	two	NUM
eurjchem-503	195	20	olefinic	olefinic	ADJ
eurjchem-503	195	21	protons	proton	NOUN
eurjchem-503	195	22	at	at	ADP
eurjchem-503	195	23			NUM
eurjchem-503	195	24	6.43	6.43	NUM
eurjchem-503	195	25	ppm	ppm	NOUN
eurjchem-503	195	26	(	(	PUNCT
eurjchem-503	195	27	dt	dt	PROPN
eurjchem-503	195	28	,	,	PUNCT
eurjchem-503	195	29	j	j	PROPN
eurjchem-503	195	30	=	=	NUM
eurjchem-503	195	31	10.1	10.1	NUM
eurjchem-503	195	32	and	and	CCONJ
eurjchem-503	195	33	1.9	1.9	NUM
eurjchem-503	195	34	hz	hz	NOUN
eurjchem-503	195	35	,	,	PUNCT
eurjchem-503	195	36	19‐h	19‐h	NUM
eurjchem-503	195	37	)	)	PUNCT
eurjchem-503	195	38	,	,	PUNCT
eurjchem-503	195	39	5.98	5.98	NUM
eurjchem-503	195	40	(	(	PUNCT
eurjchem-503	195	41	dd	dd	NOUN
eurjchem-503	195	42	,	,	PUNCT
eurjchem-503	195	43	j	j	NOUN
eurjchem-503	196	1	=	=	NOUN
eurjchem-503	196	2	10.1	10.1	NUM
eurjchem-503	196	3	and	and	CCONJ
eurjchem-503	196	4	2.3	2.3	NUM
eurjchem-503	196	5	hz	hz	NOUN
eurjchem-503	196	6	,	,	PUNCT
eurjchem-503	196	7	18‐h	18‐h	NUM
eurjchem-503	196	8	)	)	PUNCT
eurjchem-503	196	9	confirms	confirm	VERB
eurjchem-503	196	10	the	the	DET
eurjchem-503	196	11	presence	presence	NOUN
eurjchem-503	196	12	of	of	ADP
eurjchem-503	196	13	a	a	DET
eurjchem-503	196	14	d	d	PROPN
eurjchem-503	196	15	/	/	SYM
eurjchem-503	196	16	e‐cis	e‐cis	PROPN
eurjchem-503	196	17	junction	junction	NOUN
eurjchem-503	196	18	in	in	ADP
eurjchem-503	196	19	enone	enone	PROPN
eurjchem-503	196	20	,	,	PUNCT
eurjchem-503	196	21	12	12	NUM
eurjchem-503	196	22	.	.	PUNCT
eurjchem-503	197	1	the	the	DET
eurjchem-503	197	2	spectroscopic	spectroscopic	ADJ
eurjchem-503	197	3	data	data	NOUN
eurjchem-503	197	4	is	be	AUX
eurjchem-503	197	5	consistent	consistent	ADJ
eurjchem-503	197	6	with	with	ADP
eurjchem-503	197	7	our	our	PRON
eurjchem-503	197	8	previous	previous	ADJ
eurjchem-503	197	9	reports	report	NOUN
eurjchem-503	197	10	on	on	ADP
eurjchem-503	197	11	similar	similar	ADJ
eurjchem-503	197	12	systems	system	NOUN
eurjchem-503	197	13	[	[	X
eurjchem-503	197	14	23	23	NUM
eurjchem-503	197	15	]	]	PUNCT
eurjchem-503	197	16	.	.	PUNCT
eurjchem-503	198	1	we	we	PRON
eurjchem-503	198	2	considered	consider	VERB
eurjchem-503	198	3	the	the	DET
eurjchem-503	198	4	epoxidation	epoxidation	NOUN
eurjchem-503	198	5	of	of	ADP
eurjchem-503	198	6	enone	enone	PROPN
eurjchem-503	198	7	,	,	PUNCT
eurjchem-503	198	8	12	12	NUM
eurjchem-503	198	9	,	,	PUNCT
eurjchem-503	198	10	to	to	PART
eurjchem-503	198	11	build	build	VERB
eurjchem-503	198	12	the	the	DET
eurjchem-503	198	13	oxygen	oxygen	NOUN
eurjchem-503	198	14	functionality	functionality	NOUN
eurjchem-503	198	15	at	at	ADP
eurjchem-503	198	16	c‐18	c‐18	NOUN
eurjchem-503	198	17	.	.	PUNCT
eurjchem-503	199	1	reaction	reaction	NOUN
eurjchem-503	199	2	of	of	ADP
eurjchem-503	199	3	α	α	PROPN
eurjchem-503	199	4	,	,	PUNCT
eurjchem-503	199	5	β‐unsaturated	β‐unsaturate	VERB
eurjchem-503	199	6	17‐	17‐	NUM
eurjchem-503	199	7	ketone	ketone	NOUN
eurjchem-503	199	8	,	,	PUNCT
eurjchem-503	199	9	12	12	NUM
eurjchem-503	199	10	,	,	PUNCT
eurjchem-503	199	11	with	with	ADP
eurjchem-503	199	12	h2o2	h2o2	NOUN
eurjchem-503	199	13	and	and	CCONJ
eurjchem-503	199	14	sodium	sodium	NOUN
eurjchem-503	199	15	hydroxide	hydroxide	NOUN
eurjchem-503	199	16	in	in	ADP
eurjchem-503	199	17	the	the	DET
eurjchem-503	199	18	presence	presence	NOUN
eurjchem-503	199	19	of	of	ADP
eurjchem-503	199	20	methanol	methanol	NOUN
eurjchem-503	199	21	:	:	PUNCT
eurjchem-503	199	22	methylene	methylene	NOUN
eurjchem-503	199	23	dichloride	dichloride	NOUN
eurjchem-503	199	24	(	(	PUNCT
eurjchem-503	199	25	4:1	4:1	NUM
eurjchem-503	199	26	)	)	PUNCT
eurjchem-503	199	27	at	at	ADP
eurjchem-503	199	28	0‐5	0‐5	NUM
eurjchem-503	199	29	oc	oc	NOUN
eurjchem-503	199	30	for	for	ADP
eurjchem-503	199	31	one	one	NUM
eurjchem-503	199	32	and	and	CCONJ
eurjchem-503	199	33	half	half	ADJ
eurjchem-503	199	34	hours	hour	NOUN
eurjchem-503	199	35	gave	give	VERB
eurjchem-503	199	36	the	the	DET
eurjchem-503	199	37	18/19‐α‐epoxide	18/19‐α‐epoxide	NUM
eurjchem-503	199	38	,	,	PUNCT
eurjchem-503	199	39	13	13	NUM
eurjchem-503	199	40	,	,	PUNCT
eurjchem-503	199	41	in	in	ADP
eurjchem-503	199	42	86	86	NUM
eurjchem-503	199	43	%	%	NOUN
eurjchem-503	199	44	yield	yield	NOUN
eurjchem-503	199	45	.	.	PUNCT
eurjchem-503	200	1	ir	ir	PROPN
eurjchem-503	200	2	absorption	absorption	NOUN
eurjchem-503	200	3	at	at	ADP
eurjchem-503	200	4	1712	1712	NUM
eurjchem-503	200	5	cm‐1	cm‐1	NOUN
eurjchem-503	200	6	for	for	ADP
eurjchem-503	200	7	(	(	PUNCT
eurjchem-503	200	8	saturated	saturate	VERB
eurjchem-503	200	9	c	c	NOUN
eurjchem-503	200	10	=	=	NOUN
eurjchem-503	200	11	o	o	NOUN
eurjchem-503	200	12	)	)	PUNCT
eurjchem-503	200	13	and	and	CCONJ
eurjchem-503	200	14	1h	1h	NUM
eurjchem-503	200	15	nmr	nmr	NOUN
eurjchem-503	200	16	signals	signal	NOUN
eurjchem-503	200	17	at	at	ADP
eurjchem-503	200	18			NUM
eurjchem-503	200	19	3.31	3.31	NUM
eurjchem-503	200	20	ppm	ppm	NOUN
eurjchem-503	200	21	(	(	PUNCT
eurjchem-503	200	22	dd	dd	NOUN
eurjchem-503	200	23	,	,	PUNCT
eurjchem-503	200	24	j	j	NOUN
eurjchem-503	201	1	=	=	SYM
eurjchem-503	201	2	3.2	3.2	NUM
eurjchem-503	201	3	and	and	CCONJ
eurjchem-503	201	4	1.6	1.6	NUM
eurjchem-503	201	5	hz	hz	NOUN
eurjchem-503	201	6	,	,	PUNCT
eurjchem-503	201	7	19‐h	19‐h	NUM
eurjchem-503	201	8	)	)	PUNCT
eurjchem-503	201	9	and	and	CCONJ
eurjchem-503	201	10	3.43	3.43	NUM
eurjchem-503	201	11	(	(	PUNCT
eurjchem-503	201	12	dd	dd	PROPN
eurjchem-503	201	13	,	,	PUNCT
eurjchem-503	201	14	j	j	NOUN
eurjchem-503	201	15	=	=	SYM
eurjchem-503	201	16	3.6	3.6	NUM
eurjchem-503	201	17	hz	hz	NOUN
eurjchem-503	201	18	,	,	PUNCT
eurjchem-503	201	19	18‐h	18‐h	NUM
eurjchem-503	201	20	)	)	PUNCT
eurjchem-503	201	21	supported	support	VERB
eurjchem-503	201	22	the	the	DET
eurjchem-503	201	23	structure	structure	NOUN
eurjchem-503	201	24	of	of	ADP
eurjchem-503	201	25	compound	compound	NOUN
eurjchem-503	201	26	13	13	NUM
eurjchem-503	201	27	.	.	PUNCT
eurjchem-503	202	1	theα‐epoxy	theα‐epoxy	PROPN
eurjchem-503	202	2	ketone	ketone	NOUN
eurjchem-503	202	3	,	,	PUNCT
eurjchem-503	202	4	13	13	NUM
eurjchem-503	202	5	,	,	PUNCT
eurjchem-503	202	6	was	be	AUX
eurjchem-503	202	7	observed	observe	VERB
eurjchem-503	202	8	due	due	ADP
eurjchem-503	202	9	to	to	ADP
eurjchem-503	202	10	the	the	DET
eurjchem-503	202	11	convex	convex	NOUN
eurjchem-503	202	12	α‐face	α‐face	PUNCT
eurjchem-503	202	13	epoxidation	epoxidation	NOUN
eurjchem-503	202	14	[	[	X
eurjchem-503	202	15	23	23	NUM
eurjchem-503	202	16	]	]	PUNCT
eurjchem-503	202	17	.	.	PUNCT
eurjchem-503	203	1	the	the	DET
eurjchem-503	203	2	epoxide	epoxide	NOUN
eurjchem-503	203	3	13	13	NUM
eurjchem-503	203	4	was	be	AUX
eurjchem-503	203	5	allowed	allow	VERB
eurjchem-503	203	6	to	to	PART
eurjchem-503	203	7	react	react	VERB
eurjchem-503	203	8	with	with	ADP
eurjchem-503	203	9	conc	conc	X
eurjchem-503	203	10	.	.	PUNCT
eurjchem-503	203	11	sulfuric	sulfuric	PROPN
eurjchem-503	203	12	acid	acid	PROPN
eurjchem-503	203	13	(	(	PUNCT
eurjchem-503	203	14	a	a	DET
eurjchem-503	203	15	few	few	ADJ
eurjchem-503	203	16	drops	drop	NOUN
eurjchem-503	203	17	)	)	PUNCT
eurjchem-503	203	18	in	in	ADP
eurjchem-503	203	19	methanol	methanol	NOUN
eurjchem-503	203	20	and	and	CCONJ
eurjchem-503	203	21	refluxing	refluxing	NOUN
eurjchem-503	203	22	for	for	ADP
eurjchem-503	203	23	6	6	NUM
eurjchem-503	203	24	hours	hour	NOUN
eurjchem-503	203	25	in	in	ADP
eurjchem-503	203	26	an	an	DET
eurjchem-503	203	27	argon	argon	NOUN
eurjchem-503	203	28	atmosphere	atmosphere	NOUN
eurjchem-503	203	29	,	,	PUNCT
eurjchem-503	203	30	the	the	DET
eurjchem-503	203	31	required	require	VERB
eurjchem-503	203	32	18‐methoxy	18‐methoxy	NUM
eurjchem-503	203	33	enone	enone	NOUN
eurjchem-503	203	34	,	,	PUNCT
eurjchem-503	203	35	14	14	NUM
eurjchem-503	203	36	,	,	PUNCT
eurjchem-503	203	37	was	be	AUX
eurjchem-503	203	38	obtained	obtain	VERB
eurjchem-503	203	39	in	in	ADP
eurjchem-503	203	40	86	86	NUM
eurjchem-503	203	41	%	%	NOUN
eurjchem-503	203	42	yield	yield	NOUN
eurjchem-503	203	43	.	.	PUNCT
eurjchem-503	204	1	the	the	DET
eurjchem-503	204	2	structure	structure	NOUN
eurjchem-503	204	3	of	of	ADP
eurjchem-503	204	4	the	the	DET
eurjchem-503	204	5	key	key	ADJ
eurjchem-503	204	6	product	product	NOUN
eurjchem-503	204	7	14	14	NUM
eurjchem-503	204	8	was	be	AUX
eurjchem-503	204	9	established	establish	VERB
eurjchem-503	204	10	from	from	ADP
eurjchem-503	204	11	the	the	DET
eurjchem-503	204	12	following	follow	VERB
eurjchem-503	204	13	spectral	spectral	ADJ
eurjchem-503	204	14	data	datum	NOUN
eurjchem-503	204	15	;	;	PUNCT
eurjchem-503	204	16	ir	ir	PROPN
eurjchem-503	204	17	absorption	absorption	NOUN
eurjchem-503	204	18	at	at	ADP
eurjchem-503	204	19	1681	1681	NUM
eurjchem-503	204	20	cm‐1	cm‐1	NOUN
eurjchem-503	204	21	(	(	PUNCT
eurjchem-503	204	22	for	for	ADP
eurjchem-503	204	23	the	the	DET
eurjchem-503	204	24	conjugated	conjugated	ADJ
eurjchem-503	204	25	enone	enone	NOUN
eurjchem-503	204	26	)	)	PUNCT
eurjchem-503	204	27	and	and	CCONJ
eurjchem-503	204	28	1h	1h	NUM
eurjchem-503	204	29	nmr	nmr	NOUN
eurjchem-503	204	30	signal	signal	NOUN
eurjchem-503	204	31	of	of	ADP
eurjchem-503	204	32	olefinic	olefinic	ADJ
eurjchem-503	204	33	proton	proton	NOUN
eurjchem-503	204	34	at	at	ADP
eurjchem-503	204	35			NUM
eurjchem-503	204	36	5.34	5.34	NUM
eurjchem-503	204	37	ppm	ppm	NOUN
eurjchem-503	204	38	(	(	PUNCT
eurjchem-503	204	39	brs	brs	NOUN
eurjchem-503	204	40	,	,	PUNCT
eurjchem-503	204	41	19‐h	19‐h	NUM
eurjchem-503	204	42	)	)	PUNCT
eurjchem-503	204	43	.	.	PUNCT
eurjchem-503	205	1	4	4	X
eurjchem-503	205	2	.	.	X
eurjchem-503	205	3	conclusion	conclusion	NOUN
eurjchem-503	205	4	from	from	ADP
eurjchem-503	205	5	the	the	DET
eurjchem-503	205	6	viewpoint	viewpoint	NOUN
eurjchem-503	205	7	of	of	ADP
eurjchem-503	205	8	simple	simple	ADJ
eurjchem-503	205	9	procedure	procedure	NOUN
eurjchem-503	205	10	,	,	PUNCT
eurjchem-503	205	11	mild	mild	ADJ
eurjchem-503	205	12	reaction	reaction	NOUN
eurjchem-503	205	13	conditions	condition	NOUN
eurjchem-503	205	14	,	,	PUNCT
eurjchem-503	205	15	and	and	CCONJ
eurjchem-503	205	16	high	high	ADJ
eurjchem-503	205	17	yields	yield	NOUN
eurjchem-503	205	18	,	,	PUNCT
eurjchem-503	205	19	the	the	DET
eurjchem-503	205	20	present	present	ADJ
eurjchem-503	205	21	route	route	NOUN
eurjchem-503	205	22	provides	provide	VERB
eurjchem-503	205	23	a	a	DET
eurjchem-503	205	24	practical	practical	ADJ
eurjchem-503	205	25	method	method	NOUN
eurjchem-503	205	26	for	for	ADP
eurjchem-503	205	27	synthesis	synthesis	NOUN
eurjchem-503	205	28	of	of	ADP
eurjchem-503	205	29	11,18‐dimethoxy‐(20α)‐	11,18‐dimethoxy‐(20α)‐	NUM
eurjchem-503	205	30	18,19‐didehydro‐yohimban‐17‐one	18,19‐didehydro‐yohimban‐17‐one	NUM
eurjchem-503	205	31	,	,	PUNCT
eurjchem-503	205	32	14	14	NUM
eurjchem-503	205	33	,	,	PUNCT
eurjchem-503	205	34	a	a	DET
eurjchem-503	205	35	key	key	ADJ
eurjchem-503	205	36	intermediate	intermediate	NOUN
eurjchem-503	205	37	to	to	ADP
eurjchem-503	205	38	the	the	DET
eurjchem-503	205	39	total	total	ADJ
eurjchem-503	205	40	synthesis	synthesis	NOUN
eurjchem-503	205	41	of	of	ADP
eurjchem-503	205	42	(	(	PUNCT
eurjchem-503	205	43	±)‐reserpine	±)‐reserpine	X
eurjchem-503	205	44	1	1	NUM
eurjchem-503	205	45	,	,	PUNCT
eurjchem-503	205	46	the	the	DET
eurjchem-503	205	47	synthetic	synthetic	ADJ
eurjchem-503	205	48	studies	study	NOUN
eurjchem-503	205	49	towards	towards	ADP
eurjchem-503	205	50	the	the	DET
eurjchem-503	205	51	conversion	conversion	NOUN
eurjchem-503	205	52	of	of	ADP
eurjchem-503	205	53	this	this	DET
eurjchem-503	205	54	key	key	ADJ
eurjchem-503	205	55	intermediate	intermediate	ADJ
eurjchem-503	205	56	14	14	NUM
eurjchem-503	205	57	to	to	PART
eurjchem-503	205	58	(	(	PUNCT
eurjchem-503	205	59	±)‐	±)‐	ADJ
eurjchem-503	205	60	reserpine	reserpine	NOUN
eurjchem-503	205	61	are	be	AUX
eurjchem-503	205	62	in	in	ADP
eurjchem-503	205	63	progress	progress	NOUN
eurjchem-503	205	64	in	in	ADP
eurjchem-503	205	65	our	our	PRON
eurjchem-503	205	66	laboratory	laboratory	NOUN
eurjchem-503	205	67	and	and	CCONJ
eurjchem-503	205	68	will	will	AUX
eurjchem-503	205	69	be	be	AUX
eurjchem-503	205	70	published	publish	VERB
eurjchem-503	205	71	later	later	ADV
eurjchem-503	205	72	.	.	PUNCT
eurjchem-503	206	1	acknowledgements	acknowledgement	NOUN
eurjchem-503	206	2	we	we	PRON
eurjchem-503	206	3	thank	thank	VERB
eurjchem-503	206	4	professor	professor	PROPN
eurjchem-503	206	5	dr	dr	PROPN
eurjchem-503	206	6	.	.	PROPN
eurjchem-503	206	7	yoshisuke	yoshisuke	PROPN
eurjchem-503	206	8	tsuda	tsuda	NOUN
eurjchem-503	206	9	for	for	ADP
eurjchem-503	206	10	fruitful	fruitful	ADJ
eurjchem-503	206	11	discussions	discussion	NOUN
eurjchem-503	206	12	,	,	PUNCT
eurjchem-503	206	13	guidance	guidance	NOUN
eurjchem-503	206	14	and	and	CCONJ
eurjchem-503	206	15	encouragement	encouragement	NOUN
eurjchem-503	206	16	during	during	ADP
eurjchem-503	206	17	this	this	DET
eurjchem-503	206	18	research	research	NOUN
eurjchem-503	206	19	work	work	NOUN
eurjchem-503	206	20	.	.	PUNCT
eurjchem-503	207	1	higher	high	ADJ
eurjchem-503	207	2	education	education	NOUN
eurjchem-503	207	3	of	of	ADP
eurjchem-503	207	4	pakistan	pakistan	PROPN
eurjchem-503	207	5	is	be	AUX
eurjchem-503	207	6	acknowledged	acknowledge	VERB
eurjchem-503	207	7	for	for	ADP
eurjchem-503	207	8	financial	financial	ADJ
eurjchem-503	207	9	support	support	NOUN
eurjchem-503	207	10	.	.	PUNCT
eurjchem-503	208	1	references	reference	NOUN
eurjchem-503	208	2	[	[	X
eurjchem-503	208	3	1	1	NUM
eurjchem-503	208	4	]	]	PUNCT
eurjchem-503	208	5	.	.	PUNCT
eurjchem-503	209	1	muiler	muiler	PROPN
eurjchem-503	209	2	,	,	PUNCT
eurjchem-503	209	3	j.	j.	PROPN
eurjchem-503	209	4	m.	m.	PROPN
eurjchem-503	209	5	;	;	PUNCT
eurjchem-503	209	6	schlittler	schlittler	PROPN
eurjchem-503	209	7	,	,	PUNCT
eurjchem-503	209	8	e.	e.	PROPN
eurjchem-503	209	9	;	;	PUNCT
eurjchem-503	209	10	bein	bein	PROPN
eurjchem-503	209	11	,	,	PUNCT
eurjchem-503	209	12	h.	h.	PROPN
eurjchem-503	209	13	j.	j.	PROPN
eurjchem-503	209	14	experientia	experientia	PROPN
eurjchem-503	209	15	1952	1952	NUM
eurjchem-503	209	16	,	,	PUNCT
eurjchem-503	209	17	8	8	NUM
eurjchem-503	209	18	,	,	PUNCT
eurjchem-503	209	19	338‐339	338‐339	NUM
eurjchem-503	209	20	.	.	PUNCT
eurjchem-503	210	1	[	[	X
eurjchem-503	210	2	2	2	NUM
eurjchem-503	210	3	]	]	PUNCT
eurjchem-503	210	4	.	.	PUNCT
eurjchem-503	211	1	monachino	monachino	PROPN
eurjchem-503	211	2	,	,	PUNCT
eurjchem-503	211	3	j.	j.	PROPN
eurjchem-503	211	4	econ	econ	PROPN
eurjchem-503	211	5	.	.	PUNCT
eurjchem-503	212	1	bot	bot	PROPN
eurjchem-503	212	2	.	.	PUNCT
eurjchem-503	213	1	1954	1954	NUM
eurjchem-503	213	2	,	,	PUNCT
eurjchem-503	213	3	8	8	NUM
eurjchem-503	213	4	,	,	PUNCT
eurjchem-503	213	5	349‐365	349‐365	PROPN
eurjchem-503	213	6	.	.	PUNCT
eurjchem-503	214	1	[	[	X
eurjchem-503	214	2	3	3	NUM
eurjchem-503	214	3	]	]	PUNCT
eurjchem-503	214	4	.	.	PUNCT
eurjchem-503	215	1	chatterjee	chatterjee	PROPN
eurjchem-503	215	2	,	,	PUNCT
eurjchem-503	215	3	a.	a.	PROPN
eurjchem-503	215	4	;	;	PUNCT
eurjchem-503	215	5	pakrashi	pakrashi	PROPN
eurjchem-503	215	6	,	,	PUNCT
eurjchem-503	215	7	s.	s.	PROPN
eurjchem-503	215	8	;	;	PUNCT
eurjchem-503	215	9	werner	werner	PROPN
eurjchem-503	215	10	,	,	PUNCT
eurjchem-503	215	11	g.	g.	PROPN
eurjchem-503	215	12	fortschr	fortschr	PROPN
eurjchem-503	215	13	.	.	PUNCT
eurjchem-503	216	1	chem	chem	PROPN
eurjchem-503	216	2	.	.	PUNCT
eurjchem-503	217	1	org	org	PROPN
eurjchem-503	217	2	.	.	PUNCT
eurjchem-503	218	1	naturst	naturst	PROPN
eurjchem-503	218	2	.	.	PUNCT
eurjchem-503	219	1	1956	1956	NUM
eurjchem-503	219	2	,	,	PUNCT
eurjchem-503	219	3	13	13	NUM
eurjchem-503	219	4	,	,	PUNCT
eurjchem-503	219	5	346‐351	346‐351	NUM
eurjchem-503	219	6	.	.	PUNCT
eurjchem-503	220	1	[	[	X
eurjchem-503	220	2	4	4	NUM
eurjchem-503	220	3	]	]	PUNCT
eurjchem-503	220	4	.	.	PUNCT
eurjchem-503	220	5	woodson	woodson	PROPN
eurjchem-503	220	6	,	,	PUNCT
eurjchem-503	220	7	r.	r.	PROPN
eurjchem-503	220	8	e.	e.	PROPN
eurjchem-503	220	9	;	;	PUNCT
eurjchem-503	220	10	younken	younken	PROPN
eurjchem-503	220	11	,	,	PUNCT
eurjchem-503	220	12	h.	h.	PROPN
eurjchem-503	220	13	w.	w.	PROPN
eurjchem-503	220	14	;	;	PUNCT
eurjchem-503	220	15	schlittler	schlittler	PROPN
eurjchem-503	220	16	,	,	PUNCT
eurjchem-503	220	17	e.	e.	PROPN
eurjchem-503	220	18	;	;	PUNCT
eurjchem-503	220	19	schneider	schneider	PROPN
eurjchem-503	220	20	,	,	PUNCT
eurjchem-503	220	21	j.	j.	PROPN
eurjchem-503	220	22	a.	a.	PROPN
eurjchem-503	220	23	rauwolfia	rauwolfia	PROPN
eurjchem-503	220	24	:	:	PUNCT
eurjchem-503	220	25	botany	botany	NOUN
eurjchem-503	220	26	,	,	PUNCT
eurjchem-503	220	27	pharmacognosy	pharmacognosy	NOUN
eurjchem-503	220	28	,	,	PUNCT
eurjchem-503	220	29	chemistry	chemistry	NOUN
eurjchem-503	220	30	,	,	PUNCT
eurjchem-503	220	31	and	and	CCONJ
eurjchem-503	220	32	pharmacology	pharmacology	NOUN
eurjchem-503	220	33	,	,	PUNCT
eurjchem-503	220	34	little	little	ADJ
eurjchem-503	220	35	,	,	PUNCT
eurjchem-503	220	36	brown	brown	ADJ
eurjchem-503	220	37	and	and	CCONJ
eurjchem-503	220	38	co.	co.	PROPN
eurjchem-503	220	39	,	,	PUNCT
eurjchem-503	220	40	boston	boston	PROPN
eurjchem-503	220	41	,	,	PUNCT
eurjchem-503	220	42	1957	1957	NUM
eurjchem-503	220	43	.	.	PUNCT
eurjchem-503	221	1	[	[	X
eurjchem-503	221	2	5	5	NUM
eurjchem-503	221	3	]	]	PUNCT
eurjchem-503	221	4	.	.	PUNCT
eurjchem-503	222	1	lucas	lucas	PROPN
eurjchem-503	222	2	,	,	PUNCT
eurjchem-503	222	3	r.	r.	PROPN
eurjchem-503	222	4	a.	a.	PROPN
eurjchem-503	222	5	prog	prog	PROPN
eurjchem-503	222	6	.	.	PUNCT
eurjchem-503	223	1	med	med	PROPN
eurjchem-503	223	2	.	.	PROPN
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eurjchem-503	223	4	.	.	PUNCT
eurjchem-503	224	1	1963	1963	NUM
eurjchem-503	224	2	,	,	PUNCT
eurjchem-503	224	3	3	3	NUM
eurjchem-503	224	4	,	,	PUNCT
eurjchem-503	224	5	146‐186	146‐186	NUM
eurjchem-503	224	6	.	.	PUNCT
eurjchem-503	225	1	[	[	X
eurjchem-503	225	2	6	6	NUM
eurjchem-503	225	3	]	]	PUNCT
eurjchem-503	225	4	.	.	PUNCT
eurjchem-503	226	1	aube	aube	PROPN
eurjchem-503	226	2	,	,	PUNCT
eurjchem-503	226	3	j.	j.	PROPN
eurjchem-503	226	4	;	;	PUNCT
eurjchem-503	226	5	ghosh	ghosh	PROPN
eurjchem-503	226	6	,	,	PUNCT
eurjchem-503	226	7	s.	s.	PROPN
eurjchem-503	226	8	advances	advance	VERB
eurjchem-503	226	9	in	in	ADP
eurjchem-503	226	10	heterocyclic	heterocyclic	ADJ
eurjchem-503	226	11	natural	natural	ADJ
eurjchem-503	226	12	product	product	NOUN
eurjchem-503	226	13	synthesis	synthesis	NOUN
eurjchem-503	226	14	;	;	PUNCT
eurjchem-503	226	15	pearson	pearson	PROPN
eurjchem-503	226	16	,	,	PUNCT
eurjchem-503	226	17	w.	w.	PROPN
eurjchem-503	226	18	h.	h.	PROPN
eurjchem-503	226	19	,	,	PUNCT
eurjchem-503	226	20	ed	ed	NOUN
eurjchem-503	226	21	.	.	PUNCT
eurjchem-503	226	22	;	;	PUNCT
eurjchem-503	227	1	jai	jai	PROPN
eurjchem-503	227	2	(	(	PUNCT
eurjchem-503	227	3	java	java	PROPN
eurjchem-503	227	4	advanced	advanced	ADJ
eurjchem-503	227	5	imaging	imaging	NOUN
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eurjchem-503	227	7	press	press	NOUN
eurjchem-503	227	8	:	:	PUNCT
eurjchem-503	227	9	greenwich	greenwich	PROPN
eurjchem-503	227	10	,	,	PUNCT
eurjchem-503	227	11	ct	ct	PROPN
eurjchem-503	227	12	,	,	PUNCT
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eurjchem-503	227	14	.	.	PUNCT
eurjchem-503	228	1	[	[	X
eurjchem-503	228	2	7	7	NUM
eurjchem-503	228	3	]	]	PUNCT
eurjchem-503	228	4	.	.	PUNCT
eurjchem-503	228	5	szantay	szantay	PROPN
eurjchem-503	228	6	,	,	PUNCT
eurjchem-503	228	7	c.	c.	PROPN
eurjchem-503	228	8	;	;	PUNCT
eurjchem-503	228	9	honty	honty	PROPN
eurjchem-503	228	10	,	,	PUNCT
eurjchem-503	228	11	k.	k.	PROPN
eurjchem-503	229	1	monoterpenoid	monoterpenoid	PROPN
eurjchem-503	229	2	indole	indole	NOUN
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eurjchem-503	229	4	;	;	PUNCT
eurjchem-503	229	5	saxton	saxton	PROPN
eurjchem-503	229	6	,	,	PUNCT
eurjchem-503	229	7	j.	j.	PROPN
eurjchem-503	229	8	e.	e.	PROPN
eurjchem-503	229	9	,	,	PUNCT
eurjchem-503	229	10	ed	ed	PROPN
eurjchem-503	229	11	.	.	PUNCT
eurjchem-503	229	12	;	;	PUNCT
eurjchem-503	229	13	john	john	PROPN
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eurjchem-503	229	15	&	&	CCONJ
eurjchem-503	229	16	sons	sons	PROPN
eurjchem-503	229	17	,	,	PUNCT
eurjchem-503	229	18	chichester	chichester	PROPN
eurjchem-503	229	19	,	,	PUNCT
eurjchem-503	229	20	1994	1994	NUM
eurjchem-503	229	21	.	.	PUNCT
eurjchem-503	230	1	[	[	X
eurjchem-503	230	2	8	8	NUM
eurjchem-503	230	3	]	]	PUNCT
eurjchem-503	230	4	.	.	PUNCT
eurjchem-503	231	1	baxter	baxter	PROPN
eurjchem-503	231	2	,	,	PUNCT
eurjchem-503	231	3	e.	e.	PROPN
eurjchem-503	231	4	w.	w.	PROPN
eurjchem-503	231	5	;	;	PUNCT
eurjchem-503	231	6	mariano	mariano	PROPN
eurjchem-503	231	7	,	,	PUNCT
eurjchem-503	231	8	p.	p.	PROPN
eurjchem-503	231	9	s.	s.	PROPN
eurjchem-503	231	10	in	in	ADP
eurjchem-503	231	11	alkaloids	alkaloid	NOUN
eurjchem-503	231	12	:	:	PUNCT
eurjchem-503	231	13	chemical	chemical	NOUN
eurjchem-503	231	14	and	and	CCONJ
eurjchem-503	231	15	biological	biological	ADJ
eurjchem-503	231	16	perspectives	perspective	NOUN
eurjchem-503	231	17	;	;	PUNCT
eurjchem-503	231	18	pelletier	pelletier	NOUN
eurjchem-503	231	19	,	,	PUNCT
eurjchem-503	231	20	s.	s.	PROPN
eurjchem-503	231	21	w.	w.	PROPN
eurjchem-503	231	22	,	,	PUNCT
eurjchem-503	231	23	ed	ed	PROPN
eurjchem-503	231	24	.	.	PUNCT
eurjchem-503	231	25	;	;	PUNCT
eurjchem-503	231	26	springer‐verlag	springer‐verlag	PROPN
eurjchem-503	231	27	,	,	PUNCT
eurjchem-503	231	28	new	new	PROPN
eurjchem-503	231	29	york	york	PROPN
eurjchem-503	231	30	,	,	PUNCT
eurjchem-503	231	31	1992	1992	NUM
eurjchem-503	231	32	.	.	PUNCT
eurjchem-503	232	1	[	[	X
eurjchem-503	232	2	9	9	NUM
eurjchem-503	232	3	]	]	PUNCT
eurjchem-503	232	4	.	.	PUNCT
eurjchem-503	233	1	szantay	szantay	PROPN
eurjchem-503	233	2	,	,	PUNCT
eurjchem-503	233	3	c.	c.	PROPN
eurjchem-503	233	4	;	;	PUNCT
eurjchem-503	233	5	blasko	blasko	PROPN
eurjchem-503	233	6	,	,	PUNCT
eurjchem-503	233	7	g.	g.	PROPN
eurjchem-503	233	8	;	;	PUNCT
eurjchem-503	233	9	honty	honty	PROPN
eurjchem-503	233	10	,	,	PUNCT
eurjchem-503	233	11	k.	k.	PROPN
eurjchem-503	233	12	;	;	PUNCT
eurjchem-503	233	13	dornyei	dornyei	PROPN
eurjchem-503	233	14	,	,	PUNCT
eurjchem-503	233	15	g.	g.	PROPN
eurjchem-503	233	16	the	the	DET
eurjchem-503	233	17	alkaloids	alkaloid	NOUN
eurjchem-503	233	18	;	;	PUNCT
eurjchem-503	233	19	brossi	brossi	NOUN
eurjchem-503	233	20	,	,	PUNCT
eurjchem-503	233	21	a.	a.	NOUN
eurjchem-503	233	22	,	,	PUNCT
eurjchem-503	233	23	ed	ed	NOUN
eurjchem-503	233	24	.	.	PROPN
eurjchem-503	233	25	,	,	PUNCT
eurjchem-503	233	26	academic	academic	ADJ
eurjchem-503	233	27	press	press	NOUN
eurjchem-503	233	28	,	,	PUNCT
eurjchem-503	233	29	orlando	orlando	PROPN
eurjchem-503	233	30	,	,	PUNCT
eurjchem-503	233	31	1986	1986	NUM
eurjchem-503	233	32	.	.	PUNCT
eurjchem-503	234	1	[	[	X
eurjchem-503	234	2	10	10	NUM
eurjchem-503	234	3	]	]	PUNCT
eurjchem-503	234	4	.	.	PUNCT
eurjchem-503	235	1	woodward	woodward	PROPN
eurjchem-503	235	2	,	,	PUNCT
eurjchem-503	235	3	r.	r.	PROPN
eurjchem-503	235	4	b.	b.	PROPN
eurjchem-503	235	5	;	;	PUNCT
eurjchem-503	235	6	bader	bader	PROPN
eurjchem-503	235	7	,	,	PUNCT
eurjchem-503	235	8	f.	f.	PROPN
eurjchem-503	235	9	e.	e.	PROPN
eurjchem-503	235	10	;	;	PUNCT
eurjchem-503	235	11	bickel	bickel	PROPN
eurjchem-503	235	12	,	,	PUNCT
eurjchem-503	235	13	h.	h.	PROPN
eurjchem-503	235	14	;	;	PUNCT
eurjchem-503	235	15	frey	frey	PROPN
eurjchem-503	235	16	,	,	PUNCT
eurjchem-503	235	17	a.	a.	PROPN
eurjchem-503	235	18	j.	j.	PROPN
eurjchem-503	235	19	;	;	PUNCT
eurjchem-503	235	20	kierstead	kierstead	PROPN
eurjchem-503	235	21	,	,	PUNCT
eurjchem-503	235	22	r.	r.	PROPN
eurjchem-503	235	23	w.	w.	PROPN
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eurjchem-503	235	25	am	am	PROPN
eurjchem-503	235	26	.	.	PUNCT
eurjchem-503	236	1	chem	chem	PROPN
eurjchem-503	236	2	.	.	PUNCT
eurjchem-503	237	1	soc	soc	PROPN
eurjchem-503	237	2	.	.	PUNCT
eurjchem-503	238	1	1956	1956	NUM
eurjchem-503	238	2	,	,	PUNCT
eurjchem-503	238	3	78	78	NUM
eurjchem-503	238	4	,	,	PUNCT
eurjchem-503	238	5	2023‐2025	2023‐2025	NUM
eurjchem-503	238	6	.	.	PUNCT
eurjchem-503	239	1	[	[	X
eurjchem-503	239	2	11	11	NUM
eurjchem-503	239	3	]	]	PUNCT
eurjchem-503	239	4	.	.	PUNCT
eurjchem-503	240	1	woodward	woodward	PROPN
eurjchem-503	240	2	,	,	PUNCT
eurjchem-503	240	3	r.	r.	PROPN
eurjchem-503	240	4	b.	b.	PROPN
eurjchem-503	240	5	;	;	PUNCT
eurjchem-503	240	6	bader	bader	PROPN
eurjchem-503	240	7	,	,	PUNCT
eurjchem-503	240	8	f.	f.	PROPN
eurjchem-503	240	9	e.	e.	PROPN
eurjchem-503	240	10	;	;	PUNCT
eurjchem-503	240	11	bickel	bickel	PROPN
eurjchem-503	240	12	,	,	PUNCT
eurjchem-503	240	13	h.	h.	PROPN
eurjchem-503	240	14	;	;	PUNCT
eurjchem-503	240	15	kierstead	kierstead	PROPN
eurjchem-503	240	16	,	,	PUNCT
eurjchem-503	240	17	r.	r.	PROPN
eurjchem-503	240	18	w.	w.	PROPN
eurjchem-503	240	19	tetrahedron	tetrahedron	PROPN
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eurjchem-503	240	21	,	,	PUNCT
eurjchem-503	240	22	2	2	NUM
eurjchem-503	240	23	,	,	PUNCT
eurjchem-503	240	24	1‐57	1‐57	NUM
eurjchem-503	240	25	.	.	PUNCT
eurjchem-503	241	1	[	[	X
eurjchem-503	241	2	12	12	NUM
eurjchem-503	241	3	]	]	PUNCT
eurjchem-503	241	4	.	.	PUNCT
eurjchem-503	242	1	pearlman	pearlman	PROPN
eurjchem-503	242	2	,	,	PUNCT
eurjchem-503	242	3	b.	b.	PROPN
eurjchem-503	242	4	a.	a.	PROPN
eurjchem-503	242	5	j.	j.	PROPN
eurjchem-503	242	6	am	am	PROPN
eurjchem-503	242	7	.	.	PUNCT
eurjchem-503	243	1	chem	chem	NOUN
eurjchem-503	243	2	.	.	PUNCT
eurjchem-503	244	1	soc	soc	PROPN
eurjchem-503	244	2	.	.	PUNCT
eurjchem-503	245	1	1979	1979	NUM
eurjchem-503	245	2	,	,	PUNCT
eurjchem-503	245	3	101	101	NUM
eurjchem-503	245	4	,	,	PUNCT
eurjchem-503	245	5	6404‐6408	6404‐6408	NUM
eurjchem-503	245	6	.	.	PUNCT
eurjchem-503	246	1	[	[	X
eurjchem-503	246	2	13	13	NUM
eurjchem-503	246	3	]	]	PUNCT
eurjchem-503	246	4	.	.	PUNCT
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eurjchem-503	246	6	,	,	PUNCT
eurjchem-503	246	7	p.	p.	NOUN
eurjchem-503	246	8	a.	a.	NOUN
eurjchem-503	246	9	;	;	PUNCT
eurjchem-503	246	10	schaus	schaus	PROPN
eurjchem-503	246	11	,	,	PUNCT
eurjchem-503	246	12	j.	j.	PROPN
eurjchem-503	246	13	m.	m.	PROPN
eurjchem-503	246	14	;	;	PUNCT
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eurjchem-503	246	16	,	,	PUNCT
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eurjchem-503	246	19	j.	j.	PROPN
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eurjchem-503	246	21	.	.	PUNCT
eurjchem-503	247	1	chem	chem	PROPN
eurjchem-503	247	2	.	.	PUNCT
eurjchem-503	248	1	soc	soc	PROPN
eurjchem-503	248	2	.	.	PUNCT
eurjchem-503	249	1	1980	1980	NUM
eurjchem-503	249	2	,	,	PUNCT
eurjchem-503	249	3	102	102	NUM
eurjchem-503	249	4	,	,	PUNCT
eurjchem-503	249	5	6157‐6159	6157‐6159	NUM
eurjchem-503	249	6	.	.	PUNCT
eurjchem-503	250	1	[	[	X
eurjchem-503	250	2	14	14	NUM
eurjchem-503	250	3	]	]	PUNCT
eurjchem-503	250	4	.	.	PUNCT
eurjchem-503	250	5	wender	wender	PROPN
eurjchem-503	250	6	,	,	PUNCT
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eurjchem-503	250	8	a.	a.	NOUN
eurjchem-503	250	9	;	;	PUNCT
eurjchem-503	250	10	schaus	schaus	PROPN
eurjchem-503	250	11	,	,	PUNCT
eurjchem-503	250	12	j.	j.	PROPN
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eurjchem-503	250	14	;	;	PUNCT
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eurjchem-503	250	21	,	,	PUNCT
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eurjchem-503	250	23	,	,	PUNCT
eurjchem-503	250	24	263‐	263‐	NUM
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eurjchem-503	250	26	.	.	PUNCT
eurjchem-503	251	1	[	[	X
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eurjchem-503	251	3	]	]	PUNCT
eurjchem-503	251	4	.	.	PUNCT
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eurjchem-503	252	3	s.	s.	PROPN
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eurjchem-503	252	5	;	;	PUNCT
eurjchem-503	252	6	grzejszczak	grzejszczak	PROPN
eurjchem-503	252	7	,	,	PUNCT
eurjchem-503	252	8	s.	s.	PROPN
eurjchem-503	252	9	;	;	PUNCT
eurjchem-503	252	10	rueger	rueger	PROPN
eurjchem-503	252	11	,	,	PUNCT
eurjchem-503	252	12	h.	h.	PROPN
eurjchem-503	252	13	;	;	PUNCT
eurjchem-503	252	14	williamson	williamson	PROPN
eurjchem-503	252	15	,	,	PUNCT
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eurjchem-503	252	20	.	.	PUNCT
eurjchem-503	253	1	chem	chem	NOUN
eurjchem-503	253	2	.	.	PUNCT
eurjchem-503	254	1	soc	soc	PROPN
eurjchem-503	254	2	.	.	PUNCT
eurjchem-503	255	1	1985	1985	NUM
eurjchem-503	255	2	,	,	PUNCT
eurjchem-503	255	3	107	107	NUM
eurjchem-503	255	4	,	,	PUNCT
eurjchem-503	255	5	4072‐4072	4072‐4072	NUM
eurjchem-503	255	6	.	.	PUNCT
eurjchem-503	256	1	[	[	X
eurjchem-503	256	2	16	16	NUM
eurjchem-503	256	3	]	]	PUNCT
eurjchem-503	256	4	.	.	PUNCT
eurjchem-503	257	1	martin	martin	PROPN
eurjchem-503	257	2	,	,	PUNCT
eurjchem-503	257	3	s.	s.	PROPN
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eurjchem-503	257	5	;	;	PUNCT
eurjchem-503	257	6	rueger	rueger	PROPN
eurjchem-503	257	7	,	,	PUNCT
eurjchem-503	257	8	h.	h.	PROPN
eurjchem-503	257	9	;	;	PUNCT
eurjchem-503	257	10	williamson	williamson	PROPN
eurjchem-503	257	11	,	,	PUNCT
eurjchem-503	257	12	s.	s.	PROPN
eurjchem-503	257	13	a.	a.	PROPN
eurjchem-503	257	14	;	;	PUNCT
eurjchem-503	257	15	grzejszczak	grzejszczak	PROPN
eurjchem-503	257	16	,	,	PUNCT
eurjchem-503	257	17	s.	s.	PROPN
eurjchem-503	257	18	j.	j.	PROPN
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eurjchem-503	257	20	.	.	PUNCT
eurjchem-503	258	1	chem	chem	PROPN
eurjchem-503	258	2	.	.	PUNCT
eurjchem-503	259	1	soc	soc	PROPN
eurjchem-503	259	2	.	.	PUNCT
eurjchem-503	260	1	1987	1987	NUM
eurjchem-503	260	2	,	,	PUNCT
eurjchem-503	260	3	109	109	NUM
eurjchem-503	260	4	,	,	PUNCT
eurjchem-503	260	5	6124‐6136	6124‐6136	NUM
eurjchem-503	260	6	.	.	PUNCT
eurjchem-503	261	1	[	[	X
eurjchem-503	261	2	17	17	NUM
eurjchem-503	261	3	]	]	SYM
eurjchem-503	261	4	.	.	PUNCT
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eurjchem-503	261	10	.	.	PUNCT
eurjchem-503	262	1	chem	chem	PROPN
eurjchem-503	262	2	.	.	PUNCT
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eurjchem-503	263	2	,	,	PUNCT
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eurjchem-503	263	4	,	,	PUNCT
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eurjchem-503	263	6	.	.	PUNCT
eurjchem-503	264	1	yar	yar	PROPN
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eurjchem-503	264	11	(	(	PUNCT
eurjchem-503	264	12	1	1	NUM
eurjchem-503	264	13	)	)	PUNCT
eurjchem-503	264	14	(	(	PUNCT
eurjchem-503	264	15	2012	2012	NUM
eurjchem-503	264	16	)	)	PUNCT
eurjchem-503	264	17	26‐31	26‐31	ADV
eurjchem-503	264	18	31	31	NUM
eurjchem-503	265	1	[	[	X
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eurjchem-503	265	3	]	]	PUNCT
eurjchem-503	265	4	.	.	PUNCT
eurjchem-503	266	1	hanessian	hanessian	PROPN
eurjchem-503	266	2	,	,	PUNCT
eurjchem-503	266	3	s.	s.	PROPN
eurjchem-503	266	4	;	;	PUNCT
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