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Synfacts 2006(6): 0538-0538  
DOI: 10.1055/s-2006-934480
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Bipinnatin J

Contributor(s): Philip Kocienski, Thomas Snaddon
Q. Huang, V. H. Rawal*
The University of Chicago, USA
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

Pseudopterogorgia Octocorals are a fruitful source of furanocembranoid natural products. The Bipinnatin subclass possesses members with potent anticancer and neurotoxic properties. One of the simplest members, (±)-Bipinnatin J, is of interest to investigate biosynthetic routes to other Bipinnatins and related furanocembranoids. Of interest in this synthesis are (1) the Negishi cross-coupling with which to prepare C and (2) the intramolecular diastereoselective Nozaki-Hiyama-Kishi reaction of D to (±)-Bipinnatin J.