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Synfacts 2006(7): 0635-0635  
DOI: 10.1055/s-2006-941829
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Lactacystin

Contributor(s): Philip Kocienski, Fiona Black
N. Fukuda, K. Sasaki, T. V. R. S. Sastry, M. Kanai*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

(+)-Lactacystin is an irreversible inhibitor of the 20S proteosome which is involved in degradation of ubiquitinated proteins. In this total synthesis the C-5 stereocenter of the highly substituted γ-lactam core is synthesized using a catalytic enantioselective Strecker reaction.