Concise syntheses of natural diarylheptanoids containing a 1,4-pentadiene unit

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2025-05-13 DOI:10.1007/s13659-025-00517-8

Guang Tao, Xin-Yue Hu, Hong-Xing Liu, Xing-Ren Li, Li-Dong Shao, Gang Xu

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Abstract

Two concise and efficient synthetic routes were developed for the synthesis of three 1,7-diarylheptanoids (1–3) containing a 1,4-pentadiene unit, which were originally isolated from Ottelia acuminata var. acuminata. The first approach focused on the construction of linear diarylheptanoids 1 and 3 featuring a (1E,4E)-pentadiene moiety, via a Suzuki coupling reaction. The second strategy enabled the synthesis of sixteen-membered macrocyclic ether 2 with a (1Z,4E)-pentadiene unit. The challenging macrocyclization was successfully accomplished through an Ullmann coupling. Notably, the formation of the Z-olefin within the macrocyclic framework was promoted by the inherent ring strain of diarylether-type heptane system, which preferentially stabilizes this particular configuration.

Graphical Abstract

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含有1,4-戊二烯单元的天然二芳基庚烷的简明合成

为合成3个含有1,4-戊二烯单元的1,7-二芳基庚烷（1 - 3），研究了两条简洁高效的合成路线。第一种方法是通过Suzuki偶联反应构建具有(1E,4E)-戊二烯片段的线性二芳基七烷类化合物1和3。第二种策略可以合成具有(1Z,4E)-戊二烯单元的十六元大环醚2。通过乌尔曼耦合成功地完成了具有挑战性的大环化。值得注意的是，二芳醚型庚烷体系的固有环应变促进了z -烯烃在大环框架内的形成，并优先稳定了这一特殊构型。图形抽象

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.