Synthesis of Sceptrin and Ageliferin

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 .