SECONDARY METABOLITES BY CHEMICAL SCREENING - 13. ENANTIOSELECTIVE SYNTHESIS OF δ-LACTONES FROM STREPTENOL A, A CHIRAL BUILDING BLOCK FROM STREPTOMYCES

Article abstract of DOI:10.1016/S0040-4020(01)86398-5

The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enatiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described.The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group.This reaction furnishes in one step the δ-lactones 3a and 3b and requires no protecting group.