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Synfacts 2010(11): 1211-1211  
DOI: 10.1055/s-0030-1258708
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of GSK966587

Contributor(s): Philip Kocienski
E. A. Voight*, H. Yin, S. V. Downing, S. A. Calad, H. Matsuhashi, I. Giordano, A. J. Hennessy, R. M. Goodman, J. L. Wood
GlaxoSmithKline, King of Prussia, USA; GlaxoSmithKline, Stevenage, UK
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The eight-step synthesis of antibacterial agent GSK966587 (25% overall yield) ­required no protecting groups and involved only three isolated intermediates (C, G and J). Key steps were a Mizoroki-Heck reaction, a Negishi coupling, a directed ortho-metalation, and a Sharpless-Katsuki asymmetric epoxidation.