Enantioselective synthesis of a fluorinated analogue of the orsellinic acid-type twelve-membered lactone lasiodiplodin

The chemoenzymatic synthesis of the racemate and the one enantiomer of the fluorinated analogue 8 of the natural cyclooxygenase inhibitor lasiodiplodi n is decribed. A lipase-mediated deracemization of the fluorohydrin 18 prov ided the chiral, nonracemic building block for the enantioselective synthes is of the title compound. The key step was the formation of the 12-membered lactone by a ring-closing metathesis.