Synthetic studies on the mevinic acids using the chiron approach: total synthesis of (+)-dihydromevinolin

…, PJ Roy, M Petrini, PJ Hodges, R Di Fabio…

Index: Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico Journal of Organic Chemistry, 1990 ,  vol. 55,  # 22  p. 5766 - 5777

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Citation Number: 52

Abstract

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 (trimethylsily1) peroxide.