PHENOL BENZYLIC EPOXIDE TO QUINONE METHIDE ELECTRON REORGANIZATION - SYNTHESIS OF (+/-)-TAXODONE

被引:17
作者
SANCHEZ, AJ [1 ]
KONOPELSKI, JP [1 ]
机构
[1] UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM,SANTA CRUZ,CA 95064
关键词
D O I
10.1021/jo00097a057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of(+/-)-taxodone (1) is described. The C-ring is formed by the cycloaddition of methyl acrylate with furan 8, the latter derived from isodrimenin. The C13 isopropyl group was introduced via a sulfur ylide rearrangement followed by reductive cleavage. Compound I was synthesized in 61% yield by deprotection and intramolecular oxirane opening of diacetate 31 with potassium tert-butoxide and water in THF.
引用
收藏
页码:5445 / 5452
页数:8
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