Enantiospecific synthesis of (4S,5S,6S)-4,5,6-trihydroxycyclohex-2-enone and (+)-conduritol C from fluorobenzene via microbial oxidation

Epoxidation of the chiral diene 5, produced by Pseudomonas putida oxidation of fluorobenzene, gave fluoroconduritol 9 and cyclohexenone 11; the latter was used in a short synthesis of (+)-conduritol C 1.