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Synfacts 2006(9): 0871-0871  
DOI: 10.1055/s-2006-942045
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (+)-Calafianin

Contributor(s): Philip Kocienski, Thomas Snaddon
S. Bardhan, D. C. Schmitt, Jr. J. A. Porco, *
Boston University, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Noteworthy in this synthesis of (+)-Cala­fianin are (a) the enantioselective nucleophilic epoxidation of a protected quinone, (b) the 1,3-dipolar cycloaddition of nitrile oxide and olefin functions, and (c) a metal alkoxide-catalyzed ester-amide exchange reaction. Stereochemical assignment of the natural product was achieved through this endeavor.