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Synfacts 2009(3): 0237-0237  
DOI: 10.1055/s-0028-1087694
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Pinnatoxin A

Contributor(s): Philip Kocienski, Arndt W. Schmidt
S. Nakamura*, F. Kikuchi, S. Hashimoto*
Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Pinnatoxin A is a marine toxin isolated from the shellfish Pinna muricata. It is reported to be a Ca²+ channel activator, although its limited availability prevented a thorough evaluation. This synthesis features a ruthenium-catalyzed enyne macrocyclization and a late-stage thermo­lysis to generate the A-ring cyclic imine.