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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 18期

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

页码：5445 / 5452

页数：8

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