The Journal of Organic Chemistry

Synthesis of optically active butenolides via chromium alkoxycarbene complexes: total synthesis of (+)-tetrahydrocerulenin and two butenolides from the marine …

M Miller, LS Hegedus

Index: Miller, Michael; Hegedus, Louis S. Journal of Organic Chemistry, 1993 , vol. 58, # 24 p. 6779 - 6785

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Citation Number: 49

Abstract

Optically active butenolides were synthesized from the corresponding cyclobutanones, derived from the photolysis of chromium alkoxycarbene complexes and optically active ene- carbamates. The cyclobutanones were oxidized (Baeyer-Villiger) to the corresponding lactones, and subsequent baseinduced elimination of the 8-oxazolidinone ring provided optically active butenolides efficiently. The butenolides were utilized in the syntheses of (+ ...