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THE INTRAMOLECULAR CYCLOADDITION OF AZIDES WITH OMEGA-CHLOROALKENES - A FACILE ROUTE TO (-)-SWAINSONINE AND OTHER INDOLIZIDINE ALKALOIDS

被引：76
作者：
PEARSON, WH
LIN, KC
机构：
[1] Department of Chemistry, The University of Michigan, Ann Arbor
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 52期
关键词：
D O I：
10.1016/S0040-4039(00)97301-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A potentially general route to the 1-azabicyclo]n,m.O[alkane skeleton of various alkaloids is embodied in the intramolecular 1,3-dipolar cycloaddition of aliphatic azides with omega-chloroalkenes. Cycloaddition is followed by rearrangement and intramolecular N-alkylation, affording bicyclic iminium ions 1 in one operation. The application of this method to the synthesis of (+/-)-sigma-coniceine 6, (1S,2R,8aR)-indolizidine-1,2-diol 13 and (-)-swainsonine 15 is described.
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页码：7571 / 7574
页数：4
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