Catalytic, Enantioselective Synthesis of Taranabant, a Novel, Acyclic Cannabinoid-1 Receptor Inverse Agonist for the Treatment of Obesity

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• 作者：Cheng-yi Chen ; Lisa F. Frey ; Scott Shultz ; Debra J. Wallace ; Karen Marcantonio ; Joeseph F. Payack ; Enrique Vazquez ; Shawn A. Springfield ; George Zhou ; Ping Liu ; Gerard R. Kieczykowski ; Alex M. Chen ; B
• 刊名：Organic Process Research & Development
• 出版年：2007
• 出版时间：May 2007
• 年：2007
• 卷：11
• 期：3
• 页码：616 - 623
• 全文大小：180K
• 年卷期：v.11,no.3(May 2007)
• ISSN：1520-586X

文摘

Chiral amide 1 (MK-0364, taranabant) is a potent, selective,and orally bioavailable cannabinoid-1 receptor (CB-1R) inverseagonist indicated for the treatment of obesity. An asymmetricsynthesis featuring a dynamic kinetic resolution via hydrogenation for the preparation of the bromo alcohol 5 is disclosed.Conversion of the alcohol intermediate to the chiral amide 1 isaccomplished in good overall yield.