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.
Mani
Neelakandha S.
NS
Department of Chemistry, The Johns Hopkins University, Baltimore, Maryland 21218.
Townsend
Craig A.
CA