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Synfacts 2007(5): 0455-0455  
DOI: 10.1055/s-2007-968393
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Heptemerone B

Contributor(s): Philip Kocienski, Thomas Snaddon
A. K. Miller, C. C. Hughes, J. J. Kennedy-Smith, S. N. Gradl, D. Trauner*
University of California, Berkeley, USA
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

The heptemerones display potent fungicidal activity against Magnaprthe grisea, the plant pathogen responsible for rice blast disease. This convergent approach features a rare intramolecular anodic oxidative coupling of silyl enol ether and furan moieties (N to P). For a discussion of this reaction, see: D. L. Wright and co-workers J. Org. Chem. 2004, 69, 3726-3734.