THERMOSTABLE ENZYMES IN ORGANIC-SYNTHESIS .7. TOTAL SYNTHESIS OF THE WESTERN CORN-ROOTWORM SEX-PHEROMONE 8-METHYLDEC-2-YL PROPANOATE USING A TBADH-GENERATED C2-BIFUNCTIONAL CHIRON

Enantiomerically pure alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalyzed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. This advantage has been demonstrated by a total synthesis of all four isomers of 8-methyldec-2-yl propanoate, the sex pheromone emitted by the female western corn rootworm, Diabrotica virgifera virgifera LeConte. These four isomers were obtained in a very short procedure (either three or five steps) with an enantiomeric purity that exceeds 99% using a single chiral building block, (2S,8S)-(+)-2,8-dihydroxynonane. The latter diol, characterized by a synthetically useful C2 symmetry, was obtained by TBADH-catalyzed reduction of nonane-2,8-dione.