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

Article abstract of DOI:10.1021/jo00039a023

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 percent 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.