MERCURIC TRIFLUOROACETATE MEDIATED BROMINATIVE CYCLIZATIONS OF DIENES - TOTAL SYNTHESIS OF DL-3BETA-BROMO-8-EPICAPARRAPI OXIDE

被引：50
作者：
HOYE, TR
KURTH, MJ
机构：
[1] Department of Chemistry, University of Minnesota, Minneapolis
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 20期
关键词：
D O I：
10.1021/jo01334a003
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mercuric trifluoroacetate induces the electrophilic cyclization of homogeranic acid and diene alcohols 10 with concomitant carbon-carbon bond formation to generate the bicyclic organomercury compounds 2 and 12. The mercury substituent can be stereospecifically replaced by bromine with either retention or inversion of configuration to give the bromides 1 or 4 and 11 or 14, respectively. Application of this net brominative cyclization to a synthesis of dl-3β-bromo-8-epicaparrapi oxide (15) in seven steps and 12% yield from geranylacetone is described. © 1979, American Chemical Society. All rights reserved.
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页码：3461 / 3467
页数：7
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