PHOTOCYCLIZATION OF ENAMIDES .29. DEHYDROGENATION WITH BENZENESELENINIC ANHYDRIDE IN THE TOTAL SYNTHESIS OF ERGOT ALKALOIDS

被引：26

作者：

NINOMIYA, I ^{[1
]}

HASHIMOTO, C ^{[1
]}

KIGUCHI, T ^{[1
]}

NAITO, T ^{[1
]}

BARTON, DHR ^{[1
]}

LUSINCHI, X ^{[1
]}

MILLIET, P ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 03期

关键词：

D O I：

10.1039/p19900000707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Investigation of the dehydrogenative conversion of indolines into indoles with benzeneseleninic anhydride (1) resulted in the development of an efficient standardised procedure, which was successfully applied to the final steps in first total synthesis of (±)-lysergol (18), (±)-isolysergol (27), and (±)-elymoclavine (29).

引用

页码：707 / 713

页数：7

共 28 条

[1] PHOTOCYCLIZATION OF ENAMIDES .29. A GENERAL STRATEGY FOR THE SYNTHESIS OF IPECAC AND HETEROYOHIMBINE ALKALOIDS
NAITO, T
KOJIMA, N
MIYATA, O
NINOMIYA, I
INOUE, M
DOI, M
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05): : 1271 - 1280
[2] DEHYDROGENATION WITH PHENYLSELENINIC ANHYDRIDE IN THE TOTAL SYNTHESIS OF ERGOT ALKALOIDS
NINOMIYA, I
HASHIMOTO, C
KIGUCHI, T
BARTON, DHR
LUSINCHI, X
MILLIET, P
TETRAHEDRON LETTERS, 1985, 26 (35) : 4187 - 4190
[3] PHOTOCYCLIZATION OF ENAMIDES .34. A PRACTICAL TOTAL SYNTHESIS OF AROMATIC YOHIMBOID ALKALOIDS, OXOGAMBIRTANNINE AND NAUCLEFICINE
NAITO, T
KURODA, E
MIYATA, O
NINOMIYA, I
CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (09) : 2216 - 2218
[4] PHOTOCYCLIZATION OF ENAMIDES .28. A FORMAL TOTAL SYNTHESIS OF (+/-)-DESERPIDINE
NAITO, T
HIRATA, Y
MIYATA, O
NINOMIYA, I
INOUE, M
KAMIICHI, K
DOI, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (04) : 901 - 906
[5] PHOTOCYCLIZATION OF ENAMIDES .31. SYNTHESIS OF CORYNANTHE ALKALOIDS CORYNANTHEINE, HIRSUTEINE, AND THE ISOSITSIRIKINES
NINOMIYA, I
NAITO, T
MIYATA, O
SHINADA, T
WINTERFELDT, E
FREUND, R
ISHIDA, T
HETEROCYCLES, 1990, 30 (02) : 1031 - 1077
[6] TOTAL SYNTHESIS OF ERGOT ALKALOIDS, (+/-)-ELYMOCLAVINE AND (+/-)-ISOLYSERGOL
NINOMIYA, I
HASHIMOTO, C
KIGUCHI, T
HETEROCYCLES, 1984, 22 (05) : 1035 - 1038
[7] PHOTOCYCLIZATION OF ENAMIDES .22. SYNTHESES OF THE DESPYRROLE ANALOGS OF SOME ERGOT ALKALOIDS INCLUDING METHYL LYSERGATE AND ISOFUMIGACLAVINE-A
NINOMIYA, I
HASHIMOTO, C
KIGUCHI, T
NAITO, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12): : 2911 - 2917
[8] PHOTOCYCLIZATION OF ENAMIDES .35. NEW TOTAL SYNTHESES OF THE ERGOT ALKALOIDS (+/-)-CHANOCLAVINE-I AND (+/-)-ISOCHANOCLAVINE-I USING A FRAGMENTATION OF 3-AMINO ALCOHOLS
NINOMIYA, I
HABE, N
KIGUCHI, T
NAITO, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12): : 3275 - 3285
[9] PHOTOCYCLIZATION OF ENAMIDES .24. TOTAL SYNTHESIS OF (+/-)-ISOFUMIGACLAVINE-B AND (+/-)-LYSERGIC ACID
NINOMYIA, I
HASHIMOTO, C
KIGUCHI, T
NAITO, T
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (05): : 941 - 948
[10] PHOTOCYCLIZATION OF ENAMIDES .25. SYNTHESES OF DESPYRROLE ANALOGS OF ERGOT ALKALOIDS INCLUDING ELYMOCLAVINE, LYSERGOL, ISOLYSERGOL, LYSERGINE, ISOLYSERGINE, FUMIGACLAVINE, AGROCLAVINE, AND LYSERGENE
NINOMIYA, I
HASHIMOTO, C
KIGUCHI, T
NAITO, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1986, 34 (07) : 2799 - 2809

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