ASYMMETRIC-SYNTHESIS OF INDOLE ALKALOIDS FROM (L)-TRYPTOPHAN - FORMAL SYNTHESES OF (-)-KOUMINE, (-)-TABERPSYCHINE AND (-)-KOUMIDINE

被引：20

作者：

BAILEY, PD

MCLAY, NR

机构：

[1] Department of Chemistry, University of York, Heslington, York

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)79407-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of (L)-tryptophan methyl ester with methyl 4-oxobutanoate under conditions of kinetic control gave a high yield of the cis-1,3-disubstituted tetrahydro-beta-carboline (6); a simple five step procedure allowed this to be transformed into the optically pure (e.e. > 95%) bridged ketone (-)-(17), whose (+) isomer has previously been used in the syntheses of (+)-koumine (1), (+)-taberpsychine (2) & (+)-koumidine (3).

引用

页码：3895 / 3898

页数：4

共 12 条

[1] APPLICATION OF A MODIFIED PICTET-SPENGLER REACTION TO THE SYNTHESIS OF OPTICALLY-ACTIVE TETRAHYDRO-BETA-CARBOLINES, KEY INTERMEDIATES IN THE PREPARATION OF MANY INDOLE ALKALOIDS [J].