The first total synthesis of (±)-jujuyane, a cyclooctanoid natural product, was accomplished from a (5 + 3) dimerization product of oxidopyrylium ylide that forms the cyclooctanoid core structure along with inherited stereochemical bias. Selective functional group modifications of the highly oxygenated dimeric structure, followed by the tactical functional group manipulation around the eight-membered carbocyclic core, enabled the total synthesis of (±)-jujuyane, which will serve a guide for future applications of oxidopyrylium dimers to the natural product total synthesis.
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January 2015
A facile total synthesis of the reported structure for panaginsene through a trimethylenemethane (TMM) diyl mediated tandem cycloaddition reaction revealed that the spectroscopic data of the synthesized structure did not match with the data of the natural product. The total synthesis of the stereoisomer of the reported structure confirmed that the correct structure of panaginsene was the 11-epi stereoisomer of the originally proposed structure of panaginsene.
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