Total Synthesis of (+)-3-Deoxyfortalpinoid F, (+)-Fortalpinoid A, and (+)-Cephinoid H

Total Synthesis of (+)-3-Deoxyfortalpinoid F, (+)-Fortalpinoid A, and (+)-Cephinoid H
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( )-3-Deoxyfortalpinoid F、( )-Fortalpinoid A 和 ( )-Cephinoid H 的全合成

DOI:
10.1002/anie.202108034
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发表时间:
2021
期刊:
Angewandte Chemie International Edition
影响因子:
--
通讯作者:
Hu Xiangdong
Hu Xiangdong
中科院分区:
其他
文献类型:
--
作者:
Ren Zhiqiang;Sun Zhongliu;Li Yifei;Fan Xin;Dai Mingda;Wang Yunxia;Hu Xiangdong

文献摘要

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3-Deoxyfortalpinoid F、fortalpinoid A和cephinoid H是红豆杉二萜类天然产物,具有多种化学结构和重要的生物活性。   我们在此报告的发展的非对映选择性Pauson-Khand反应作为一个有效的途径,以获得核心四环骨架,这是广泛存在于Cephalotaxus二萜。此外,我们能够通过闭环复分解/消除方案构建托品部分。基于此策略,首次实现了标题化合物的不对称合成。
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.