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Synthesis of Taranabant
D. J. Wallace*, K. R. Campos*, C. S. Schultz*, A. Klapars, D. Zewge, B. R. Crump, B. D. Phenix, J. C. McWilliams, S. Krska, Y. Sun, C.-y. Chen, F. Spindler
Merck Research Laboratories, Rahway, USA and Solvias AG, Basel, Switzerland
25 May 2009 (online)
Taranabant is a potential selective inverse agonist of the cannabinoid-1 receptor which is implicated in the regulation of feeding behaviour. Hence, taranabant is being developed for the treatment of obesity. The synthesis depicted incorporates three key features: (1) a simple highly stereoselective synthesis of the vinyl tosylate (A → B); (2) an efficient synthesis of a tetrasubstituted enamide by palladium-catalyzed amidation (B → D); and (3) a highly efficient asymmetric hydrogenation to create two adjacent stereogenic centers in a single step (E → G).