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Enantioselective, biocatalytic reduction of 3-substituted cyclopentenones: application to the asymmetric synthesis of an hNK-1 receptor antagonist
Authors:Campos Kevin R  Klapars Artis  Kohmura Yoshinori  Pollard David  Ishibashi Hideaki  Kato Shinji  Takezawa Akihiro  Waldman Jacob H  Wallace Debra J  Chen Cheng-yi  Yasuda Nobuyoshi
Affiliation:Department of Process Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA. kevin_campos@merck.com
Abstract:A convergent and enantioselective route to the hNK-1 receptor antagonist (1) is described, which sets all six stereogenic centers with high diastereoselectivity and delivers 1 in only 11 steps and 23% overall yield. The process was enabled by the development of the enantioselective enzymatic reduction of 3-functionalized cyclopentenones and stereospecific Pd-catalyzed etherification coupling of fragments 6 and 7.
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