Enantioselective enzyme-catalyzed transesterification of the tricyclic diol (I) with vinyl acetate (II) provides the chiral monoacetate (III). After protection of the free hydroxyl group of (III) as the tert-butyldimethylsilyl ether (IV), alkaline hydrolysis of the acetate ester group yields alcohol (V), which is then oxidized to the corresponding ketone (VI) by means of pyridinium dichromate. Finally, thermal retro-Diels-Alder reaction of (VI) under diminished pressure furnishes the target cyclopentenone derivative.