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

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[22] SYNTHESIS OF ERYTHRINA AND RELATED ALKALOIDS .29. REACTION OF PHENYLSELENENYL CHLORIDE WITH DELTA-2-ERYTHRINANS IN METHANOL - CONFORMATIONAL FLUCTUATION AND STEREOCHEMICAL PATHWAY
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[23] STUDIES IN MYCOLOGICAL CHEMISTRY .29. TOTAL SYNTHESIS OF (+/-)-O-METTHYLAVERSIN [(+/-)-TRI-O-METHYLVERSICOLORIN B] - STRUCTURE OF AVERSIN
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[24] THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION (INOC) ROUTE TO THE ERGOT ALKALOIDS - USE OF THE ISOXAZOLINE TO GAMMA-AMINO ALCOHOL CONVERSION IN THE TOTAL SYNTHESIS OF (+)-PALICLAVINE
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[25] INTERMOLECULAR AND INTRAMOLECULAR HETERO-DIELS-ALDER REACTIONS .29. SYNTHESIS OF STRICTOSIDINE ANALOGS BY HETERO-DIELS-ALDER REACTION AND THEIR BIOMIMETIC TRANSFORMATION TO INDOLE ALKALOIDS
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[26] STUDIES IN CYCLOHEPTANE SERIES .29. FRIEDEL-CRAFTS REACTION OF ANHYDRIDE OF ALPHA,BETA-DIPHENYLGLUTARIC ACID WITH AROMATIC-HYDROCARBONS AND SYNTHESIS OF SIMPLE AND SUBSTITUTED BENZ-2,3-DIPHENYLCYCLOHEPTANES
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[27] New routes to clavine-type ergot alkaloids.: Part 1.: First total synthesis of three natural products:: (+)setoclavine, (+)-isosetoclavine, (-)9,10-dihydroisosetoclavine, and structure correction of the latter
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[28] Experiments towards the synthesis of the ergot alkaloids and related structures.: Part 8.: The total synthesis of 4-methyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinoline-2-carbonitrile hydrochloride hemihydrate, an immediate precursor of the despyrrole analogues of lysergic acid and its amides
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