Gordon C. Lawrence

Reduction of bicyclo[3.2.0] hept-2-en-6-one and 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one using dehydrogenase enzymes and the fungus mortierella ramanniana

Bicyclo[3.2.0]hept-2-en-6-one (1) was reduced with an alcohol dehydrogenase from Thermoanaerobium brockii and a whole cell system (M. ramanniana) with excellent substrate enantioselectivity: 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one (2) was similarly reduced using the 3α,20β-hydroxysteroid dehydrogenase from Streptomyces hydrogenans while M. ramanniana furnished both 6S-alcohols (4a), (6b) with high optical purity.

Microbial hydroxylation of cyclohexylcyclohexane:Synthesis of an analogue of leukotriene-B3

Summary Cyclohexylcyclohexane was transformed into cyclohexylcyclohexanediols using selected fungi: 4,4′-cyclohexylcyclohexanediol was converted into an analogue of leukotriene-B 3 .

Resolution of 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one using Mortierella ramanniana and 3α,20β-hydroxy-steroid dehydrogenase, photochemistry of 3-hydroxy-7,7-dimethylbicyclo[3.2.0]heptan-6-ones, and the synthesis of (+)-eldanolide

The fungus Mortierella ramanniana reduced 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one (1) to give the (6S)-endo-alcohol (9) and the (6S)-exo-alcohol (10). In contrast the enzyme 3α,20β-hydroxy-steroid dehydrogenase was found to give the (6S)-endo-alcohol (9) and recovered optically active ketone. Both processes produced the alcohol (9) in high optical purity. The (6S)-endo-alcohol (9) was converted into the lactone (+)-(4) a late stage synthon for the pheromone eldanolide (+)-(11).