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Synfacts 2009(11): 1184-1184  
DOI: 10.1055/s-0029-1218025
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Brevenal

Contributor(s): Philip Kocienski
H. Takamura, S. Kikuchi, Y. Nakamura, Y. Yamagami, T. Kishi, I. Kadota*, Y. Yamamoto
Okayama University and Tohoku University, Sendai, Japan
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

Brevenal is a non-toxic brevetoxin antagonist that significantly improves tracheal mucus velocity in an animal model of asthma. The scheme above shows three triumphs of the synthesis: (1) the introduction of the angular methyl group at C12 (A → B), (2) the creation of ring D by an intramolecular allylation of an oxonium ion (C → D), and (3) the creation of ring E via a ring-closing metathesis reaction (D → E).