Journal of Organic Chemistry p. 3631 - 3636 (1992)
Update date:2022-08-04
Topics:
Keinan, Ehud
Sinha, Subhash C.
Sinha-Bagchi, Anjana
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.
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Doi:10.1007/s00775-012-0969-x
(2013)Doi:10.1021/ja00040a063
(1992)Doi:10.1016/j.tet.2012.11.009
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(2013)Doi:10.1016/j.tetlet.2012.11.030
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