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. 2008 Jan 3;10(1):149-52.
doi: 10.1021/ol702806v. Epub 2007 Dec 12.

Biomimetic synthesis of the shimalactones

Vladimir Sofiyev  1 , Gabriel Navarro, Dirk Trauner
Affiliations

Biomimetic synthesis of the shimalactones

Vladimir Sofiyev et al. Org Lett. .

Abstract

A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl beta-ketolactone and a Stille coupling/8pi-6pi electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.

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