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Divergent total syntheses of five illudalane sesquiterpenes and assignment of the absolute configuration
Zhixiong Zeng1, Yifan Zhao, Yandong Zhang
1Department of Chemistry and Key Laboratory of Chemical Biology of Fujian Province, iChEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China. ydzhang@xmu.edu.cn.
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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