Divergent Total Synthesis of Euphoranginol C, Euphoranginone D,ent-Trachyloban-3 beta-ol,ent-Trachyloban-3-one, Excoecarin E, andent-16 alpha-Hydroxy-atisane-3-one

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 reac...

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Published inAngewandte Chemie International Edition Vol. 59; no. 45; pp. 19919 - 19923
Main 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
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 02.11.2020
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
terpenoids
ATISANE-TYPE DITERPENOIDS
REARRANGEMENTS
cyclization
PROTONATION
natural products
ENT-KAURANE DITERPENOIDS
asymmetric synthesis
CONSTRUCTION
1ST TOTAL-SYNTHESIS
total synthesis
ENANTIOSELECTIVE TOTAL-SYNTHESIS
ALKALOIDS
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202009128