Facile and efficient syntheses of (7 <i>Z</i> ,11 <i>Z</i> )-hexadecadienyl acetate and (7 <i>Z</i> ,11 <i>E</i> )-hexadecadienyl acetate: sex pheromone components of <i>Pectinophora gossypiella</i> (Lepidoptera: Gelechiidae)
(7<i>Z</i>,11<i>Z</i>)-Hexadecadienyl acetate (<i>Z</i>7<i>Z</i>11-16:OAc) (<b>1</b>) and its geometric isomer (7<i>Z</i>,11<i>E</i>)-hexadecadienyl acetate (<i>Z</i>7<i>E</i>11-16:OAc) (<b>2</b>) have been conclusively identified as the sex pheromone of <i>Pectinophora gossypiella</i> (Lepidoptera: Gelechiidae). Pheromone-based mass trapping and mating disruption have significantly reduced <i>P gossypiella</i> populations across global cotton production areas. Synthesis of these two active components from commercially available starting materials, 2-(3-bromopropyl)-1,3-dioxolane, DHP, and 7-bromoheptyl acetate, is reported. The pivotal step involves constructing a <i>cis</i> double bond via the Wittig reaction and preparing a <i>trans</i> enol through DHP (3,4-2H-dihydropyran) ring opening. Our results provide a facile and efficient way to obtain active insect pheromones.
Authors
- Jiayue Liu (ORCID: https://orcid.org/0000-0003-0853-8158)
- S. F. Zhang
- Jiaxing Fang
- Huihui Liu (ORCID: https://orcid.org/0000-0001-7943-9566)
- Xiangbo Kong (ORCID: https://orcid.org/0000-0002-4289-3172)
- Wen-Hao Zhang
- Fu Liu
- Si-Yan Wang
- Xin Zhen
Institutions
- Anhui Agricultural University (CN)
- Chinese Academy of Medical Sciences & Peking Union Medical College (CN)
- Chinese Academy of Forestry (CN)
- Institute of Forest Ecology, Environment and Protection (CN)
- Experimental Center of Forestry in North China (CN)
Publication Details
- Journal
- Journal of Asian Natural Products Research
- Published
- 2026-03-14
- DOI
- https://doi.org/10.1080/10286020.2026.2630000
- Primary Topic
- Insect Pheromone Research and Control
- Type
- article
- Field-Weighted Citation Impact
- 0.00