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

• Published in: Angewandte 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
• Language: English
• 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

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...