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Synfacts 2008(10): 1018-1018  
DOI: 10.1055/s-2008-1078283
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

A Synthesis of Callipeltoside A

Contributor(s): Philip Kocienski
D. A. Evans*, J. D. Burch, E. Hu, G. Jaeschke
Harvard University, Cambridge, USA
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

This synthesis established the absolute stereochemistry of callipeltoside A, a marine macrolide with cytotoxicity towards human bronchopulmonary non-small-cell lung carcinoma. A very efficient vinylogous aldol reaction catalyzed by BOX ligand K created the stereocenter at C13 and the trisubstituted alkene in H.