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Updated: Dec 31, 2025

Synthesis and Mass Spectrometry Analysis of Oligo-peptoids
Published on: February 21, 2018
Total Synthesis of (-)-Pepluanol B: Conformational Control of the Eight-Membered-Ring System
Jing Zhang1, Meng Liu1, Chuanhua Wu1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, Gansu, P. R. China.
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.
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