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Synfacts 2006(12): 1202-1202  
DOI: 10.1055/s-2006-955595
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Lactacystin

Contributor(s): Philip Kocienski, Fiona Black
E. P. Balskus, E. N. Jacobsen*
Harvard University, Cambridge, USA
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Publikationsverlauf

Publikationsdatum:
22. November 2006 (online)

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Significance

A catalytic enantioselective conjugate addition reaction between cyanoacetate derivative B and a β-silyl unsaturated imide A was developed for the construction of the γ-lactone ring of (+)-lactacystin. An unusual spiro β-lactone intermediate was synthesized to activate a carboxylic acid towards attack by N-acetyl-l-cysteine.