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Synfacts 2007(8): 0782-0782
DOI: 10.1055/s-2007-968712
DOI: 10.1055/s-2007-968712
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (-)-Hennoxazole A
T. E. Smith*, W.-H. Kuo, V. D. Bock, J. L. Roizen, E. P. Balskus, A. B. Theberge
Williams College, Williamstown, USA
Further Information
Publication History
Publication Date:
24 July 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200708/lookinside/thumbnails/10.1055-s-2007-968712-1.jpg)
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.