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Synfacts 2008(7): 0673-0673  
DOI: 10.1055/s-2008-1077867
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Exiguolide

Contributor(s): Philip Kocienski, Stewart Eccles
M. S. Kwon, S. K. Woo, S. W. Na, E. Lee*
Seoul National University, Korea
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Publication History

Publication Date:
20 June 2008 (online)

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Significance

Exiguolide is isolated from the sponge Geodia exigua and has the interesting biological activity of stopping gamete fertilization but not embryogenesis in fertilized eggs of sea urchins. Noteworthy in the synthesis is the formation of the two tetrahydropyran rings by a radical (A → B) and Prins (C → D) cyclization.