Synthesis of enantiomerically enriched 2-heptanol and 3-octanol by microbial reductases ofCurvularia falcata andMucor species

Abstract

Certain insects produce 2-heptanol or 3-octanol in various glandular secretions and recent studies have shown that the 3-octanol of two different genera of ants (Crematogaster andMyrmica) can be either the (S)-(+) or mainly the (R)-(-) enantiomer, respectively. Synthesis of each of these alcohols can be achieved in relatively high enantiomeric purity by certain microbial reductases. The corresponding ketone of each alcohol is reduced byCurvularia falcata, giving an alcohol which is about 90% the (S)-(+) enantiomer, and twoMucor species give as much as 80% the (R)-(-) enantiomer. The synthesis of certain chiral alcohols from their corresponding ketones by microbial reductases can offer a simple procedure for obtaining sufficient amounts of these substances for certain behavioral studies.