Journal
ORGANIC LETTERS
Volume 10, Issue 1, Pages 149-152Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol702806v
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- NIGMS NIH HHS [R01 GM067636] Funding Source: Medline
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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/8 pi-6 pi 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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