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Synthesis 2010(12): 2039-2042  
DOI: 10.1055/s-0029-1218771
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical and Convenient Synthesis of the Protease Inhibitor Epibestatin

Anja Richter, Christian Hedberg*
Max-Planck Institute of Molecular Physiology, Department of Chemical Biology, Otto-Hahn-Strasse 11, 44227 Dortmund, Germany
Fax: +49(231)1332498; e-Mail: Christian.Hedberg@mpi-dortmund.mpg.de;
Further Information

Publication History

Received 14 January 2010
Publication Date:
05 May 2010 (online)

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Abstract

A convenient synthesis of the protease inhibitor epibestatin, a useful component in protease inhibition cocktails for use in proteomics research, is described. The synthesis sequence consists of seven steps, starting from phenylacetaldehyde, yielding enantiopure epibestatin in 8% overall yield. A regioselective Mitsunobu­ transformation of a diol is the key step in the sequence.

Key words

amino acids - asymmetric synthesis - osmium - dihydroxylation - Mitsunobu reaction

    References

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7

The structural verification of 5 was based on the characteristic 2D NMR cross peaks (COSY, HMBC) after conversion of the azide functionality into the corresponding N-acetamide derivative.