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

• DOI: 10.1007/s13659-025-00517-8
• Publication Date: 2025-05-13T06:33:04Z
• Authors: Guang Tao; Xin-Yue Hu; Hong-Xing Liu; Xing-Ren Li; Li-Dong Shao; Gang Xu

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