Enantioselective Synthesis of Four Isomers of 3-Hydroxy-4-Methyltetradecanoic Acid, the Constituent of Antifungal Cyclodepsipeptides W493 A and B

Abstract

Four possible stereoisomers of 3-hydroxy-4-methyltetradecanoic acid were enantioselectively synthesized by using Sharpless epoxidation and a subsequent epoxide-ring opening reaction with trimethylaluminum as the key steps. The absolute configuration of the β-oxyacid component of antifungal cyclodepsipeptides W493 A and B was consequently determined as 3S,4R.