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Synfacts 2008(7): 0671-0671  
DOI: 10.1055/s-2008-1077858
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Phorboxazole A

Contributor(s): Philip Kocienski, Stewart Eccles
A. B. Smith, III*, T. M. Razler, J. P. Ciavarri, T. Hirose, T. Ishikawa, R. M. Meis
University of Pennsylvania, Philadelphia, USA
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

Phorboxazole A is an extremely cytotoxic agent with a mean GI50 value of 1.58 × 10-9 across the National Cancer Institute’s panel of human cancer cell lines. Phorboxazole A was isolated from the extracts of a sponge (Phorbas sp.) found in the Indian ocean. The synthesis utilizes chemistry from the first-generation synthesis (J. Am. Chem. Soc. 2001, 123, 4834) but improves upon it sufficiently to produce gram quantities.