TANDEM CARBONYL ENE CYCLIZATION-CYCLOALKYLATION - A ROUTE TO TRIFLUOROMETHYL DITERPENOIDS

被引：14

作者：

ABOUABDELLAH, A ^{[1
]}

BONNETDELPON, D ^{[1
]}

机构：

[1] CTR ETUD PHARMACEUT,BIOCIS,CNRS,F-92296 CHATENAY MALABRY,FRANCE

来源：

TETRAHEDRON | 1994年 / 50卷 / 41期

关键词：

TRIFLUOROMETHYL KETONES; ENE-CYCLIZATION; LEWIS ACIDS; DITERPENOIDS;

D O I：

10.1016/S0040-4020(01)89305-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new sequential carbonyl-ene cyclizatian/cycloalkylation of trifluoromethyl ketones catalyzed by aluminum Lewis acids is described. From ketone 1, the 4-CF3-4-OH cis-octahydrophenanthrene 6 is obtained in 50 % yield. From ketone 2, with MeAlCl(2) a total stereoselective route to the 4-CF3-trans-10-methyl podocarpatrienol 8 (90 % yield) has been found. These studies also exhibited some striking results in the stereochemical outcome of ene cyclizations.

引用

页码：11921 / 11932

页数：12

共 26 条

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