SYNTHETIC STUDIES ON THE MEVINIC ACIDS USING THE CHIRON APPROACH - TOTAL SYNTHESIS OF (+)-DIHYDROMEVINOLIN

被引:54
作者
HANESSIAN, S
ROY, PJ
PETRINI, M
HODGES, PJ
DIFABIO, R
CARGANICO, G
机构
[1] Department of Chemistry, Universite de Montreal, Montreal, QC, Box 6128, Station A
关键词
D O I
10.1021/jo00309a022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general strategy for the synthesis of the mevinic acids starting from L-glutamic acid as a chiral template is presented. The octahydronaphthalene ring system of dihydromevinolin and mevinolin is constructed from an intramolecular Diels-Alder cycloaddition involving a butenolide. The lactone portion is elaborated from a cyclopentanone by a Baeyer-Villiger oxidation with bis(trimethylsilyl) peroxide. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:5766 / 5777
页数:12
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