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Synfacts 2007(8): 0782-0782  
DOI: 10.1055/s-2007-968712
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Hennoxazole A

Contributor(s): Philip Kocienski, Thomas Snaddon
T. E. Smith*, W.-H. Kuo, V. D. Bock, J. L. Roizen, E. P. Balskus, A. B. Theberge
Williams College, Williamstown, USA
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

(-)-Hennoxazole A is active against herpes simplex virus. This synthesis features (1) an aldol reaction, (2) a Wittig-Still rearrangement to prepare a trisubstituted Z-alkene (F), and (3) fragment linkage via a challenging intermolecular bisoxazole alkylation. For a discussion of the bisoxazole alkylation, see: T. E. Smith, E. P. Bals­kus Heterocycles 2002, 57, 1219.