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Synfacts 2007(5): 0460-0460  
DOI: 10.1055/s-2007-968394
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Bipinnatin J and (+)-Intricarene

Contributor(s): Philip Kocienski
P. A. Roethle, P. T. Hernandez, D. Trauner*
University of California, Berkeley, USA
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

A key step in the synthesis of (+)-intricarene is the transannular [5+2] cycloaddition of the oxidopyrylium intermediate H. The synthesis supports the postulate that (-)-bipinnatin J is the biogenetic precursor to intricarene. Roethle and Trauner (Org. Lett. 2006, 8, 345-347) and Huang and Rawal (Org. Lett. 2006, 8, 543-545) recently reported related syntheses of racemic bipinnatin J.