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Synfacts 2008(5): 0450-0450  
DOI: 10.1055/s-2008-1072699
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Hennoxazole A

Contributor(s): Philip Kocienski
T. E. Smith*, W.-H. Kuo, E. P. Balskus, V. D. Bock, J. L. Roizen, A. B. Theberge, K. A. Carroll, T. Kurihara, J. D. Wessler
Williams College, Williamstown, USA
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Publikationsdatum:
23. April 2008 (online)

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Significance

Hennoxazole A is a sponge metabolite with antiviral and analgesic activity. A key feature of the synthesis shown below (the fourth reported to date) is the late-stage metalation-alkylation of the methyloxazole L, a step for which choice of base is important.