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Synfacts 2006(6): 0544-0544  
DOI: 10.1055/s-2006-934492
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Sceptrin and Ageliferin

Contributor(s): Philip Kocienski, Thomas Snaddon
P. S. Baran*, K. Li, D. P. O’Malley, C. Mitsos
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

(-)-Sceptrin and (-)-Ageliferin display potent antiviral properties. Baran and co-workers previously disclosed a synthesis of racemic Sceptrin (J. Am. Chem. Soc. 2004, 126, 3726-3727) and its conversion into Ageliferin ­(Angew. Chem. Int. Ed. 2004 , 43, 2674-2677) based upon an unusual oxaquadricyclane fragmentation to prepare the all-trans cyclobutane core of the former. This same group has now disclosed an enantioselective pathway to these molecules by programmed fragmentation of enantioenriched oxaquadricyclane E.