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

Author:
Zeng, Zhixiong, Zhao, Yifan, Zhang, Yandong
Source:
Chemical communications 2019 v.55 no.29 pp. 4250-4253
ISSN:
1364-548X
Subject:
cycloaddition reactions, methylation, moieties, regioselectivity, sesquiterpenoids, synthesis
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.
Agid:
6363371