Stereoselective tetrahydropyrido[2,1-a]isoindolone synthesis via carbanionic and radical intermediates:: a model study for the Tacaman alkaloid D/E ring fusion

被引：17

作者：

Hunter, R ^{[1
]}

Richards, P ^{[1
]}

机构：

[1] Univ Cape Town, Dept Chem, ZA-7701 Cape Town, South Africa

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 19期

基金：

新加坡国家研究基金会;

关键词：

radical and carbanionic cyclisation; indole alkaloid; isoindolone synthesis;

D O I：

10.1016/S0040-4039(00)00485-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective cyclisation of melic acid-derived alpha-sulfanyllactam (1) via radical and carbanionic intermediates affords stereo-defined tetrahydropyrido[2,1-a]isoindolones as model compounds for the D/E cis-ring fusion of the Tacaman indole alkaloid skeleton. A transition-state model to explain the stereoselectivity is presented. (C) 2000 Elsevier Science Ltd. All rights reserved.

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收藏

页码：3755 / 3758

页数：4

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