Enantioselective, Biocatalytic Reduction of 3-Substituted Cyclopentenones: Application to the Asymmetric Synthesis of an hNK-1 Receptor Antagonist

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• 作者：Kevin R. Campos ; Artis Klapars ; Yoshinori Kohmura ; David Pollard ; Hideaki Ishibashi ; Shinji Kato ; Akihiro Takezawa ; Jacob H. Waldman ; Debra J. Wallace ; Cheng-yi Chen ; Nobuyoshi Yasuda
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：March 4, 2011
• 年：2011
• 卷：13
• 期：5
• 页码：1004-1007
• 全文大小：752K
• 年卷期：v.13,no.5(March 4, 2011)
• ISSN：1523-7052

文摘

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.