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Synfacts 2006(4): 0308-0308  
DOI: 10.1055/s-2006-932033
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a β-Lactam Proteasome Inhibitor

Contributor(s): Philip Kocienski
P. C. Hogan, E. J. Corey*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

Salinosporamide and Omuralide are natural β-lactone proteasome inhibitors whose use in cancer chemotherapy is limited by their instability in serum. The β-lactam G is a proteasome inhibitor which is much more stable. The key step in the Harvard synthesis is an asymmetric [2+2] cycloaddition.