STRUCTURAL AND STEREOCHEMICAL COURSE OF IN VITRO EPOXY OLEFIN CYCLIZATION . DITERPENOID INTERMEDIATES

被引:54
作者
GOLDSMITH, DJ
PHILLIPS, CF
机构
[1] Department of Chemistry, Emory University, Atlanta
关键词
D O I
10.1021/ja01049a028
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cyclization of unsaturated epoxides to tricyclic systems is shown to be a stereospecific process. Boron fluoride etherate treatment of an epoxy olefin with a central trans-substituted double bond, trans-7, leads to two tricyclic alcohols, 12 and 14, both of which have trans-fused A/B rings. The corresponding cis compound, cis-7, produces an A/B cis-fused alcohol, 20. These reactions also yield monocyclized products of specific geometry depending on the stereochemistry of the original double bond and the conformational folding of the epoxy olefin chain. The stereochemistry of these products suggests that cyclization occurs via intermediate cations of fixed geometry rather than as a “nonstop” process. © 1969, American Chemical Society. All rights reserved.
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页码:5862 / +
页数:1
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