Reduction of bicyclo [3.2.0] hept-2-en-6-one with dehydrogenase enzymes in whole cell preparations of some fungi and yeasts

Abstract

(±)-Bicyclo [3.2.0] hept-2-en-6-one (1) was reduced using a variety of fungi and yeasts. Bakers' yeast gave 6-exo-(1R,5S,6S)-bicyclo [3.2.0] hept-2-en-6-ol (2a) and 6-endo-(1S,5R,6S)-bicyclo[3.2.0]-hept-2-en-6-ol (3b) while Curvularia lunata and Mortierella ramanniana gave only the 6-endo-alcohol (3b) and optically active bicycloheptenone (1a). Under slightly modified reaction conditions (±)-6-endo-bicyclo [3.2.0] hept-2-en-6-ol was oxidized by bakers' yeast to give (1S,5R)-bicyclo [3.2.0] hept-2-en-6-one (1b) and the endo-alcohol (3a).