Synthesis of Optically Active Butenolides via Chromium Alkoxycarbene Complexes: Total Synthesis of (+)-Tetrahydrocerulenin and Two Butenolides from the Marine Sponge Plakortis lita

Article abstract of DOI:10.1021/jo00076a044

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 base-induced elimination of the β-oxazolidinone ring provided optically active butenolides efficiently.The butenolides were utilized in the syntheses of (+)-tetrahydrocerulenin and two marine natural products.