ENANTIOSPECIFIC SYNTHESES OF INDOLIZIDINE-167B AND INDOLIZIDINE-209D

被引：68

作者：

JEFFORD, CW

WANG, JB

机构：

[1] Department of Organic Chemistry, University of Geneva

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 19期

关键词：

BETA-AMINO ACID; PYRROLE; RHODIUM ACETATE; CATALYTIC HYDROGENATION;

D O I：

10.1016/S0040-4039(00)93394-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Indolizidine 209D (2) was synthesized in 11 steps from L-aspartic acid (3) in an overall yield of 16%. 3R-pyrrolylnonanoic acid, prepared from 3, was converted into the alpha-keto diazomethyl derivative, which on Rh2(OAc)4-catalyzed cyclization and catalytic hydrogenation gave 2. A similar procedure, starting from 3, afforded 3R-pyrrolyl-hexanoic acid, an intermediate which had prevoiusly been converted in 3 steps to indolizidine 167B.

引用

页码：3119 / 3122

页数：4

共 16 条

[1] INTERACTION OF GEPHYROTOXIN AND INDOLIZIDINE ALKALOIDS WITH THE NICOTINIC ACETYLCHOLINE RECEPTOR-ION CHANNEL COMPLEX OF TORPEDO ELECTROPLAX [J].