Dienes as chiral templates : easy access to pure (2S,3S,4R)-4-hydroxy-2,3-epoxycyclohex-5-en-1-one

Abstract The title compound 6 was obtained stereospecifically through a concise sequence including a Diels-Alder reaction with the chiral diene 2 and the retro reaction. The Favorskii rearrangement starting from the intermediate epoxide 4 was found to be regioselective.