Total Synthesis of (−)‐Pepluanol B: Conformational Control of the Eight‐Membered‐Ring System
| Autor: | Ran Fang, Xingang Xie, Jing Zhang, Chuanhua Wu, Lin Zhou, Peiqi Chen, Meng Liu, Huilin Li, Gaoyuan Zhao, Xuegong She |
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| Rok vydání: | 2020 |
| Předmět: |
Cyclopropanes
Bicyclic molecule 010405 organic chemistry Cyclopropanation Stereochemistry Diol Molecular Conformation Epoxide Total synthesis Stereoisomerism General Medicine General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Cyclopropane Bridged Bicyclo Compounds chemistry.chemical_compound Ring-closing metathesis chemistry Aldol reaction Cyclization Diterpenes |
| Zdroj: | Angewandte Chemie International Edition. 59:3966-3970 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201915876 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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