USE OF BIOLOGICAL SYSTEMS FOR THE PREPARATION OF CHIRAL MOLECULES IV : A TWO-STEP CHEMOENZYMATIC SYNTHESIS OF A NATURAL PHEROMONE (4R,5S)-(-)-4-METHYL 5-HYDROXY HEPTAN 3-ONE, SITOPHILURE.

Article abstract of DOI:10.1016/S0040-4039(00)96689-9

Reduction of 4-methyl heptan 3,5-dione 2 by resting cells of Geotrichum candidum provides natural sitophilure (4R,5S)-(-)-4-methyl 5-hydroxy heptan 3-one 1 under anaerobic conditions.Diastereoisomer (4S,5S)-(+)-4-methyl 5-hydroxy heptan 3-one 1a is obtained under aerobic conditions.Starting β-diketone is easily obtained by a one-pot synthesis.Good yield and high enantiomeric excess are obtained for the natural pheromone.