Biomimetic synthesis of the shimalactones.
Org Lett
Department of Chemistry, University of California Berkeley, Berkeley, California 94720-1460, USA.
Published: January 2008
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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