The Journal of Organic Chemistry

Stereocontrolled synthesis of exocyclic trisubstituted double bonds by stereospecific iminium ion-vinylsilane cyclizations. A short synthetic route to indoloquinolizidine …

LE Overman, TC Malone

Index: Overman, Larry E.; Malone, Thomas C. Journal of Organic Chemistry, 1982 , vol. 47, # 27 p. 5297 - 5300

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Citation Number: 37

Abstract

The reaction of (2)-and (E)-trisubstituted vinylsilanes 9 and 10 with paraformaldehyde and acid proceeded with> 98% retention of configuration to give indoloquinolizidines 13 and 3 in excellent yield. This is the first demonstration that iminium ion-vinylsilane cyclizations occur with complete retention of configuration with either vinylsilane stereoisomer. The simple indole alkaloid dl-deplancheine (3) was prepared in a stereocontrolled fashion in 26% ...