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Synfacts 2006(5): 0417-0417  
DOI: 10.1055/s-2006-934392
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 11-Acetoxy-4-deoxyasbestinin D

Contributor(s): Philip Kocienski, Thomas Snaddon
M. T. Crimmins*, J. M. Ellis
University of North Carolina at Chapel Hill, USA
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

Isolated from Briareum asbestinum in 1990, 11-acetoxy-4-deoxyasbestinin D displays significant cytotoxic and antimicrobial activity. Crimmins and Ellis employed a ring-closing metathesis/intramolecular Diels-Alder cycloaddition strategy to synthesize the oxonene ring and hydroisobenzofuran system, respectively, providing the first chemical synthesis of any member of this family of cembranoids and thus establishing their absolute configuration. A related synthesis of Ophirin B and Astrogorgin has appeared recently: M. T. Crimmins, B. H. Brown, H. R. Plake J. Am. Chem. Soc. 2006, 128, 1371-1378.