Biomimetic synthesis of the shimalactones |
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| Authors: | Sofiyev Vladimir Navarro Gabriel Trauner Dirk |
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| Institution: | Department of Chemistry, University of California Berkeley, Berkeley, California 94720-1460, USA. |
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| 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 oxabicyclo2.2.1]heptane and bicyclo4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups. |
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