ENANTIOSELECTIVE SYNTHESIS OF PUMILIOTOXIN-251D - A STRATEGY EMPLOYING AN ALLENE-BASED ELECTROPHILE-MEDIATED CYCLIZATION

被引：106

作者：

FOX, DNA

LATHBURY, D

MAHON, MF

MOLLOY, KC

GALLAGHER, T

机构：

[1] UNIV BATH,SCH CHEM,BATH BA2 7AY,AVON,ENGLAND

[2] UNIV BATH,XRAY CRYSTALLOG UNIT,BATH BA2 7AY,AVON,ENGLAND

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 07期

关键词：

D O I：

10.1021/ja00007a044

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective synthesis of pumiliotoxin 251D (1) (nine steps, 6.3% overall yield) is described in which the Pd(II)-mediated cyclization of the optically pure allenic amine 6 to give pyrrolidine 7a plays a central role. The functionality that the allene moiety imparts to 7a allows for rapid transformation to the enantiomerically pure bicyclic lactam 9. A stereocontrolled aldol elimination sequence was carried out on 9 to establish the geometry of the exocyclic alkene of 1.

引用

页码：2652 / 2656

页数：5

共 82 条

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