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Synfacts 2006(11): 1093-1093  
DOI: 10.1055/s-2006-949395
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of BMS 184394

Contributor(s): Philip Kocienski
J. G. Kim, P. J. Walsh*
University of Pennsylvania, Philadelphia, USA
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

BMS 184394 is α β,γ-selective ligand for the retinoic acid nuclear receptor. Its synthesis is used to showcase the first one-pot method for the catalytic asymmetric addition to aldehydes of organozinc reagents generated in situ to give diarylmethanols. The use of cheap bromo­arenes rather than costly arylzinc or arylboronic acids as starting materials is a significant practical advantage. Kim and Walsh report 14 examples of Ar2Zn addition (yield typically >90%, er > 9:1) and 17 examples of ArZnBu addition (yields 55-98%, er = 3:1 to 99:1) mediated by Nugent’s MIB ligand (see: Y. K. Chen, S.-J. Jeon, P. J. Walsh, W. A. Nugent Org. Synth. 2005, 82, 87-92).