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Synfacts 2008(7): 0670-0670  
DOI: 10.1055/s-2008-1077869
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 11-Acetoxy-4-deoxyasbestinin D

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

Publication Date:
20 June 2008 (online)

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Significance

Asbestinin-12 and 11-acetoxy-
4-deoxyasbestinin D are secondary metabolites of gorgonian octocoral. 11-Acetoxy-4-deoxyasbesti­nin displays cytotoxicity against CHO-K1 cells and antimicrobial activity against Klebsiella pneumoniae. A highly stereoselective Diels-Alder cycloaddition is used as the key step to form the hydroisobenzo­furan F. Asbestinine 12, which has an extra acet­oxy group at C-4, is also synthesized from ketone G following similar chemistry.