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Synfacts 2010(1): 0013-0013  
DOI: 10.1055/s-0029-1218260
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Bestatin

Contributor(s): Philip Kocienski
W.-J. Liu, B.-D. Lv, L.-Z. Gong*
University of Science and Technology of China, Hefei, P. R. of China
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

(-)-Bestatin is a peptide antibiotic from Streptomyces olivoreticuli that inhibits aminopeptidase B. It activates macrophages and T-lymphocytes and is used clinically in cancer chemotherapy. A highly enantioselective Darzens ­reaction between α-diazoacetanilide and aliphatic and aromatic aldehydes was used to synthesize (-)-bestatin and the taxol side chain.