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Synfacts 2006(6): 0539-0539  
DOI: 10.1055/s-2006-934481
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Bipinnatin J

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

Publication Date:
19 May 2006 (online)

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Significance

(±)-Bipinnatin J is a furanocembranoid isolated from gorgonian corals. It displays potent activity against various cancer cell lines and the Plasmodium falciparum parasite responsible for malaria. The key step in this synthesis is the intramolecular diastereoselective Nozaki-Hiyama-Kishi reaction of F to (±)-Bipinnatin J. For a similar synthesis of (±)-Bipinnatin J (see: Q. Huang, V. H. Rawal Org. Lett. 2006, 8, 543-545; see also: P. Kocienski, T. Snaddon Synfacts 2006, 538).