SYNTHESIS OF THE ASPIDOSPERMA SKELETON THROUGH ALLYLSILANE N-ACYLIMINIUM CYCLIZATION

被引：20

作者：

MITTENDORF, J ^{[1
]}

HIEMSTRA, H ^{[1
]}

SPECKAMP, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM,ORGAN CHEM LAB,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON | 1990年 / 46卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(01)90540-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereoselective synthesis of the Aspidosperma ring system is described, based on a combination of two stereocontrolled processes. The first features a base-catalyzed cyclization of the imine 5 to generate the indoline 4. The second involves the formation of tetracycle 2 by the ring closure of N-acyliminium ion 3, whereby an allylsilane moiety functions as π-nucleophile. © 1990.

引用

页码：4049 / 4062

页数：14

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