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.
               
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