Enantioselective, biocatalytic reduction of 3-substituted cyclopentenones: application to the asymmetric synthesis of an hNK-1 receptor antagonist |
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| 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 |
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| Affiliation: | Department of Process Chemistry, Merck Research Laboratories, Rahway, New Jersey 07065, USA. kevin_campos@merck.com |
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| 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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