90359-39-0

Upstream product

• 141667-28-9 (2S,8R)-(+)-2-(Propanoyloxy)non-8-yl p-Toluenesulfonate 
• 141667-25-6 (2S,8S)-(+)-2-(Propanoyloxy)-8-hydroxynonane 
• 141667-22-3 (2S,8S)-(+)-dihydroxynonane 
• 90410-63-2 propionate of (2S,8R)-8-methyl-2-decanol 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 
• 90359-38-9 (2R,8R)-(-)-8-methyldecan-2-ol 

Relevant academic research and scientific papers

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 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.