Cyclizations of unsymmetrical bis-1,2-(3-indolyl)ethanes: Synthesis of (-)-tjipanazole F1

被引:28
作者
Gilbert, EJ [1 ]
Ziller, JW [1 ]
VanVranken, DL [1 ]
机构
[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92697
关键词
D O I
10.1016/S0040-4020(97)01036-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The inter- and intramolecular dimerization of 3-substituted indoles was studied. The rate and extent of dimerization depends on the indole substituents The intramolecular dimerization of unsymmetrical bis-1,2-(3-indolyl)ethanes could be controlled using either thermodynamic reaction conditions (neat trifluoroacetic acid) or kinetic conditions (2 equiv acid/chloroform). This control of regiochemistry has been applied to an efficient synthesis of (-)-jipanazole F1. (C) 1997 Elsevier Science Ltd.
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页码:16553 / 16564
页数:12
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