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

doi:10.1007/s13659-025-00517-8

Natural Products and Bioprospecting ›› 2025, Vol. 15 ›› Issue (4): 32-32.DOI: 10.1007/s13659-025-00517-8

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

Guang Tao¹, Xin-Yue Hu^2,3, Hong-Xing Liu², Xing-Ren Li², Li-Dong Shao¹, Gang Xu²

1. Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650500, China;
2. State Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China;
3. University of Chinese Academy of Sciences, Beijing, 100049, China

Received:2025-03-20 Accepted:2025-04-23 Online:2025-05-13 Published:2025-08-23
Supported by:
This study was supported financially by Yunnan Key Laboratory Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan (APR202301); Yunnan Revitalization Talent Support Program "Innovation Team" Project (202305AS350014), and Foundation of DR. PLANT.

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

Guang Tao¹, Xin-Yue Hu^2,3, Hong-Xing Liu², Xing-Ren Li², Li-Dong Shao¹, Gang Xu²

1. Yunnan Key Laboratory of Southern Medicinal Utilization, School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650500, China;
2. State Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China;
3. University of Chinese Academy of Sciences, Beijing, 100049, China

通讯作者: Xing-Ren Li, E-mail:lixingren@mail.kib.ac.cn;Li-Dong Shao, E-mail:shaolidong@ynucm.edu.cn;Gang Xu, E-mail:xugang008@mail.kib.ac.cn
基金资助:
This study was supported financially by Yunnan Key Laboratory Screening and Research on Anti-pathogenic Plant Resources from Western Yunnan (APR202301); Yunnan Revitalization Talent Support Program "Innovation Team" Project (202305AS350014), and Foundation of DR. PLANT.

Abstract

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.

Key words: Diaryheptanoids, Concise synthesis, 1,4-Pentadiene, Macrocyclization

摘要： 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.

关键词: Diaryheptanoids, Concise synthesis, 1,4-Pentadiene, Macrocyclization

Guang Tao, Xin-Yue Hu, Hong-Xing Liu, Xing-Ren Li, Li-Dong Shao, Gang Xu. Concise syntheses of natural diarylheptanoids containing a 1,4-pentadiene unit[J]. Natural Products and Bioprospecting, 2025, 15(4): 32-32.

Guang Tao, Xin-Yue Hu, Hong-Xing Liu, Xing-Ren Li, Li-Dong Shao, Gang Xu. Concise syntheses of natural diarylheptanoids containing a 1,4-pentadiene unit[J]. 应用天然产物, 2025, 15(4): 32-32.

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

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

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