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Total Synthesis of (−)‐Pepluanol B: Conformational Control of the Eight‐Membered‐Ring System
Authors:Jing Zhang  Meng Liu  Chuanhua Wu  Gaoyuan Zhao  Peiqi Chen  Lin Zhou  Xingang Xie  Ran Fang  Huilin Li  Xuegong She
Abstract:The first total synthesis of the Euphorbia diterpenoid pepluanol B in both racemic and enantioenriched form involves 20 steps from a known bicyclic diol. This synthesis features an unprecedented bromo‐epoxidation to control the eight‐membered‐ring conformation. In addition, salient reactions for the construction of the tetracyclic backbone include a sterically challenging aldol reaction to establish the quaternary center, a ring closing metathesis (RCM) to forge the eight‐membered ring, and a diastereoselective cyclopropanation to assemble the embedded cyclopropane motif.
Keywords:conformational control  diterpenoids  epoxides  natural products  total synthesis
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