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.

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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
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article

Facile and efficient syntheses of (7 Z ,11 Z )-hexadecadienyl acetate and (7 Z ,11 E )-hexadecadienyl acetate: sex pheromone components of Pectinophora gossypiella (Lepidoptera: Gelechiidae)

Jiayue Liu, S. F. Zhang, Jiaxing Fang, Huihui Liu et al.
Journal of Asian Natural Products Research
Insect Pheromone Research and Control
article

Facile and efficient syntheses of (7 Z ,11 Z )-hexadecadienyl acetate and (7 Z ,11 E )-hexadecadienyl acetate: sex pheromone components of Pectinophora gossypiella (Lepidoptera: Gelechiidae)

Jiayue Liu, S. F. Zhang, Jiaxing Fang, Huihui Liu, Xiangbo Kong, Wen-Hao Zhang, Fu Liu, Si-Yan Wang, Xin Zhen
article en

Abstract

(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.

Journal of Asian Natural Products Research
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)
Openalex Percentile: Top 28%
Insect Pheromone Research and Control
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