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

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(trimethylsilyl) peroxide