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Synfacts 2010(5): 0513-0513  
DOI: 10.1055/s-0029-1219645
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of BMS-561392

Contributor(s): Philip Kocienski
N. A. Magnus*, S. Campagna, P. N. Confalone, S. Savage, D. J. Meloni, R. E. Waltermire, R. G. Wethman, M. Yates
Bristol-Myers Squibb Company, New Brunswick, USA
Further Information

Publication History

Publication Date:
22 April 2010 (online)

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Significance

Tumor necrosis factor-α (TNF-α) is a cytokine associated with acute and chronic inflammation. BMS-561392 selectively inhibits ­tumor necrosis factor-α convertase (TACE), an enzyme which generates TNF-α from its progenitor. BMS-561392 is a lead for the treatment of rheumatoid arthritis. The key step in the synthesis is the diastereoselective α-amination of the enolate E using 1-chloro-1-nitroso-cyclopentane as the electrophile.