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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 22期

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.

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页码：5766 / 5777

页数：12

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