Tetrahedron

A convergent asymmetric synthesis of γ-butenolides

M Renard, LA Ghosez

Index: Renard, Marc; Ghosez, Leon A. Tetrahedron, 2001 , vol. 57, # 13 p. 2597 - 2608

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Citation Number: 30

Abstract

The addition of aldehydes to the new enantiomerically pure lithiated sulfoxide-orthoester 13 yielded γ-butenolides of high enantiomeric purities after elimination of phenylsulfinic acid. The cyclocondensation with ketones was less stereoselective. This new asymmetric synthesis of γ-butenolides has been applied to a convergent preparation of the antifungal antibiotic (+)-cerulenin.