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Synfacts 2008(1): 0009-0009  
DOI: 10.1055/s-2007-992391
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of Omuralide

Contributor(s): Philip Kocienski, Zofia Komsta
C. B. Gilley, M. J. Buller, Y. Kobayashi*
University of California at San Diego, la Jolla, USA
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

Omuralide is a β-lactone derived from the bacterial metabolite lactacystin. It is a ­selective and potent irreversible inhibitor of the 20S proteasome and therefore a candidate for the treatment of cancer. This formal synthesis features a stereoselective Ugi reaction involving isocyanide F. For a total synthesis of omuralide, see: E. J. Corey and co-workers Angew. Chem. Int. Ed. 1998, 37, 1676.