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Synfacts 2006(3): 0196-0196  
DOI: 10.1055/s-2006-931920
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Colombiasin A and(-)-Elisapterosin B

Contributor(s): Philip Kocienski, Thomas Snaddon
A. Boezio, E. R. Jarvo, B. M. Lawrence, E. N. Jacobsen*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

Jacobsen and co-workers employed a highly regio- and diastereoselective Cr-catalyzed Diels-Alder reaction to construct enol ether D, a key intermediate in a synthesis of (-)-Colombiasin A and (-)-Elisapterosin B, bioactive natural products from the gorgonian coral Pseudopterogorgia elisabethae. For other syntheses of (-)-Colombiasin A employing quinone ­Diels-Alder reactions see: K. C. Nicolaou et al. Angew. Chem. Int. Ed. 2001, 40, 2482-2486; A. I. Kim, S. D. Rychnovsky Angew. Chem. Int. Ed. 2003, 42, 1267-1270. For use of an intramolecular variant en route to (-)-Elisapterosin B see: V. H. Rawal et al. J. Am. Chem. Soc. 2003, 125, 13022-13023.