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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
Author(s) -
Xu ZeJun,
Zong Yan,
Qiao YaNan,
Zhang JiaoZhen,
Liu Xuyuan,
Zhu MingZhu,
Xu Yuliang,
Zheng Hongbo,
Fang Liyuan,
Wang Xiaoning,
Lou HongXiang
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202009128
Subject(s) - cyclopropane , cyclopropanation , nucleophile , stereochemistry , chemistry , moiety , geraniol , regioselectivity , bicyclic molecule , octane , total synthesis , ring (chemistry) , organic chemistry , catalysis , chromatography , essential oil
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 [3.2.1.0 2,7 ]‐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.