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Total Synthesis of (+)‐3‐Deoxyfortalpinoid F, (+)‐Fortalpinoid A, and (+)‐Cephinoid H
Author(s) -
Ren Zhiqiang,
Sun Zhongliu,
Li Yifei,
Fan Xin,
Dai Mingda,
Wang Yunxia,
Hu Xiangdong
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202108034
Subject(s) - tropone , moiety , ring closing metathesis , total synthesis , stereochemistry , chemistry , metathesis , ring (chemistry) , salt metathesis reaction , natural product , combinatorial chemistry , organic chemistry , polymerization , polymer
3‐Deoxyfortalpinoid F, fortalpinoid A, and cephinoid H are members of the Cephalotaxus diterpenoids class of natural products, which feature diverse chemical structures and valuable biological activities. We report herein the development of a diastereoselective Pauson–Khand reaction as an effective pathway to access the core tetracyclic skeleton, which is found widely in Cephalotaxus diterpenoids. Furthermore, we enabled the construction of the tropone moiety through a ring‐closing metathesis/elimination protocol. Based on the developed strategy, asymmetric synthesis of the title compounds has been achieved for the first time.