Catalytic, Enantioselective Synthesis of Taranabant, a Novel, Acyclic Cannabinoid-1 Receptor Inverse Agonist for the Treatment of Obesity
Organic Process Research & Development2007Vol. 11(3), pp. 616–623
Citations Over TimeTop 10% of 2007 papers
Cheng‐yi Chen, Lisa Frey, Scott Shultz, Debra J. Wallace, Karen Marcantonio, Joeseph F. Payack, Enrique Vázquez, Shawn A. Springfield, George Zhou, Ping Liu, G. R. KIECZYKOWSKI, Alex M. Chen, Brian D. Phenix, Utpal Singh, Jeff Strine, Brianne Izzo, Shane W. Krska
Abstract
Chiral amide 1 (MK-0364, taranabant) is a potent, selective, and orally bioavailable cannabinoid-1 receptor (CB-1R) inverse agonist indicated for the treatment of obesity. An asymmetric synthesis 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 is accomplished in good overall yield.
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