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- Title
Divergent Total Synthesis of Euphoranginol C, Euphoranginone D, ent‐Trachyloban‐3β‐ol, ent‐Trachyloban‐3‐one, Excoecarin E, and ent‐16α‐Hydroxy‐atisane‐3‐one.
- Authors
Xu, Ze‐Jun; Zong, Yan; Qiao, Ya‐Nan; Zhang, Jiao‐Zhen; Liu, Xuyuan; Zhu, Ming‐Zhu; Xu, Yuliang; Zheng, Hongbo; Fang, Liyuan; Wang, Xiao‐ning; Lou, Hong‐Xiang
- Abstract
A divergent synthetic approach to biogenetically related diterpenoids such as ent‐kauranes, ent‐trachylobanes, ent‐beyerane, and ent‐atisane has been developed. The unified synthetic route involves the De Mayo reaction to rapidly generate the bicyclo[3.2.1]‐octane moiety of ent‐kaurane. The key reactions also include bioinspired nucleophilic cyclopropanation generating the [3.2.1.02,7]‐tricyclic core of ent‐trachylobane and regioselective cyclopropane fragmentation furnishing ent‐beyerane and ent‐atisane through the nucleophilic attack and protonation of the cyclopropane ring. This strategy enables the asymmetric total syntheses of six diterpenoids from the commercially available geraniol.
- Subjects
ASYMMETRIC synthesis; MOIETIES (Chemistry); DITERPENES; CYCLOPROPANATION; PROTON transfer reactions; CYCLOPROPANE derivatives
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 45, p20091
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202009128