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

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

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月13日

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

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.

Graphical Abstract