Enantioselective synthesis of (-)-idiospermuline

被引：67

作者：

Overman, LE ^{[1
]}

Peterson, EA ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

TETRAHEDRON | 2003年 / 59卷 / 35期

基金：

美国国家卫生研究院;

关键词：

cyclotryptamine alkaloids; dialkylation; Heck cyclization; vicinal quaternary centers;

D O I：

10.1016/S0040-4020(03)00855-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective total synthesis of the nonacyclic polypyrrolidinoindoline (-)-idiospermuline is described. Stereocontrolled formation of the vicinal quaternary carbon centers is achieved in a single step by dialkylation of an unsymmetrical prostereogenic dienolate with a tartrate-derived chiral dielectrophile. A catalyst-controlled diastereoselective Heck cyclization is employed to form the diaryl-substituted quaternary center. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：6905 / 6919

页数：15

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