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(+)-3-去氧紫堇宾 F、(+)-紫堇宾 A 和(+)-头孢因 H 的全合成。

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

机构信息

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education College of Chemistry & Materials Science, Northwest University, Xi'an, 710127, China.

出版信息

Angew Chem Int Ed Engl. 2021 Aug 16;60(34):18572-18576. doi: 10.1002/anie.202108034. Epub 2021 Jul 16.

Abstract

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.

摘要

3-脱氧紫堇醇 F、紫堇醇 A 和 Cephinoid H 是三尖杉二萜类天然产物的成员,具有多样的化学结构和有价值的生物活性。我们在此报告了一种非对映选择性的 Pauson-Khand 反应的发展,该反应是一种有效的方法,可以获得广泛存在于三尖杉二萜类化合物中的四环核心骨架。此外,我们通过闭环复分解/消除方案实现了对 Tropone 部分的构建。基于所开发的策略,首次实现了标题化合物的不对称合成。

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