Total Synthesis of (−)‐Pepluanol B: Conformational Control of the Eight‐Membered‐Ring System
Jing Zhang, Meng Liu, Chuanhua Wu, Gaoyuan Zhao, Peiqi Chen, Ling Zhou, Xingang Xie, Ran Fang, Huilin Li, X. 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.
Topics & Concepts
Ring (chemistry)ChemistryTotal synthesisStereochemistryOrganic chemistryBioactive Natural Diterpenoids ResearchMarine Sponges and Natural ProductsSynthetic Organic Chemistry Methods