meso-exo-3,5-dihydroxymethylenetricyclo[5.2.1.0(2,6)]decane was efficiently desymmetrized by the lipase from Pseudomonas cepacia (PS-C 'Amano' II) in vinyl acetate in high yields (93%) and with excellent enantiomeric excesses (ee > 99% by chiral GC). Chiral synthons for asymmetric synthesis were synthesized from this enantiopure compound.
lipases; enzymatic catalysis; desymmetrization; chiral compounds