AN UNEXPECTED REVERSAL IN THE STEREOCHEMISTRY OF TRANSANNULAR CYCLIZATIONS - A STEREOSELECTIVE SYNTHESIS OF (+/-)-EPILUPININE

被引：31

作者：

EDSTROM, ED

机构：

[1] Department of Chemistry and Biochemistry, Utah State University, Logan

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 41期

关键词：

TRANSANNULAR CYCLIZATIONS; QUINOLIZIDINE AND INDOLIZIDINE SYNTHESIS; EPILUPININE;

D O I：

10.1016/S0040-4039(00)93536-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transannular cyclizations of N-benzylhexahydroazec-5-en-2-one and N-benzylhexahydroazon-5-en-2-one using iodine or phenylselenenyl bromide affords substituted quinolizidines and indolizidines, respectively. In the case of the ten-membered ring lactams an unexpected reversal in stereochemistry was observed. These results were confirmed by elaboration of the iodo cycloadduct 4a into (+/-)-epilupinine.

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页码：5709 / 5712

页数：4

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