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<p>A simple and efficient approach was developed for the synthesis of 13-methyl-(5<i>Z</i>,8<i>Z</i>)-tridecadienolide (<b>1</b>) using commercially available starting materials, such as 5-hexynol (<b>2</b>) and methyl 5-hexynoate (<b>7</b>). The key intermediate, Tos-protected methyl diynoate (<b>8</b>), was stable in the crude oil and was obtained by coupling <b>7</b> with TBS- and Tos-protected oct-2-yne-1,7-diol (<b>6</b>), the latter being derived from 5-hexynol (<b>2</b>) through a series of reactions including Dess–Martin oxidation, Grignard reaction, TBS-protection, hydroxymethylation, and Tos-protection. Deprotection of the TBS group and the subsequent ester hydrolysis of intermediate <b>8</b> led to the diynoate precursor <b>9</b>. This precursor was then converted into macrolide <b>1</b> through lactonization using the Yonemitsu method, achieving an overall yield of 30.7%.</p>

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A Simple and Efficient Strategy for the Total Synthesis of 13-Methyl-(5Z,8Z)-Tridecadienolide

  • 期刊论文

  • 发表日期：

    2025年3月26日

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  • Xianrong Cai,
  • Juan Tang,
  • Jie Xiang,
  • Jia Zheng,
  • Yingwei Wang,
  • Xingyong Liang,
  • Chunru Cheng,
  • Yi Liu

摘要

A simple and efficient approach was developed for the synthesis of 13-methyl-(5Z,8Z)-tridecadienolide (1) using commercially available starting materials, such as 5-hexynol (2) and methyl 5-hexynoate (7). The key intermediate, Tos-protected methyl diynoate (8), was stable in the crude oil and was obtained by coupling 7 with TBS- and Tos-protected oct-2-yne-1,7-diol (6), the latter being derived from 5-hexynol (2) through a series of reactions including Dess–Martin oxidation, Grignard reaction, TBS-protection, hydroxymethylation, and Tos-protection. Deprotection of the TBS group and the subsequent ester hydrolysis of intermediate 8 led to the diynoate precursor 9. This precursor was then converted into macrolide 1 through lactonization using the Yonemitsu method, achieving an overall yield of 30.7%.