A Concise Synthesis of (+)-Cerulenin from a Chiral Oxiranyllithium

(+)-Cerulenin, a potent fungal inactivator of fatty acid synthases, has been prepared in optically pure form by a sequence involving reaction of a chiral oxiranyllithium with (4E,7E)-nonadienal. Synthesis of the former takes advantage of a particularly favorable Sharpless epoxidation and metalation to a configurationally stable organolithium, while the latter is available in quantity by a direct and improved route.