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Synfacts 2010(8): 0865-0865
DOI: 10.1055/s-0030-1257741
DOI: 10.1055/s-0030-1257741
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of BMS-587101
A. J. DelMonte*, R. E. Waltermire, Y. Fan, D. D. McLeod, Z. Gao, K. D. Gesenberg, K. P. Girard, M. Rosingana, X. Wang, J. Kuehne-Willmore, A. D. Braem, J. A. Castoro
Bristol-Myers Squibb Company, New Brunswick, USA
Further Information
Publication History
Publication Date:
22 July 2010 (online)
Significance
BMS-587101 inhibits the interaction between leukocyte function-associated antigen-1 (LFA-1) and the intercellular adhesion molecule (ICAM), thereby offering a potential treatment for various autoimmune and inflammatory diseases, such as rheumatoid arthritis and psoriasis. A four-step multikilogram route to BMS-587101 (22% overall yield ) from the commercial hydantoin B features an efficient dipolar cycloaddition of an azomethine ylide generated by reaction of glycine with hexamethylenetetramine (HMTA).