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Divergent total syntheses of five illudalane sesquiterpenes and assignment of the absolute configuration.

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Concise, divergent total syntheses of five bioactive illudalane sesquiterpenes have been achieved. Our synthesis features an intermolecular [2+2+2] cycloaddition, and a lactone-directed aromatic C-H oxygenation to generate a temporary phenolic… Click to show full abstract

Concise, divergent total syntheses of five bioactive illudalane sesquiterpenes have been achieved. Our synthesis features an intermolecular [2+2+2] cycloaddition, and a lactone-directed aromatic C-H oxygenation to generate a temporary phenolic hydroxyl group which enables regioselective methylation. Furthermore, the absolute configuration of radulactone was assigned by chemical synthesis.

Keywords: total syntheses; syntheses five; divergent total; illudalane sesquiterpenes; absolute configuration

Journal Title: Chemical communications
Year Published: 2019

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