Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Stereoselective Synthesis of (Z,Z)-3,13-Octadecadien-1-yl Acetate, and Its (E,Z)-Isomer, the Sex Pheromone of the Cherry Tree Borer, Synanthedon hector Butler

  • Kang, Suk-Ku (Department of Chemistry, Sung Kyun Kwan University, Natural Sceince Campus) ;
  • Park, Sun-Ku (Department of Chemistry, Sung Kyun Kwan University, Natural Sceince Campus)
  • Published : 1988.06.20
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Abstract

A mixture of (Z,Z)-3,13-octadecadien-1-yl acetate(1) and its (E,Z)-isomer(2), the sex pheromone of the cherry tree borer, Synanthedon hector Butler was synthesized. (Z)-11-Octadecen-1-al(3) was prepared from 1,10-decandiol. The Wittig reaction the above aldehyde3 with carboethoxymethylenetriphenylphosphorane, or the Wadsworth-Emmons reaction of the above aldehyde3 with the anion of triethylphosphonoacetate gave ethyl (Z,Z)-2,13-octadecadienoate and its (E,Z)-isomer. Deconjugative protonation of ethyl (Z,Z)-2,13-octadecadienoate and its (E,Z)-isomer with potassium hexamethyldisilazide followed by aqueous ammonium chloride work-up afforded stereoselectiv디y ethyl (E,Z)-3,13-octadecadienoate and its (Z,Z)-isomer, respectively, of which stereoselectivity was adjusted to give the product in the required ratio. Exposure of the above deconjugated ester to excess lithium aluminium hydride resulted in formation of the penultimate (Z,Z)-3,13-octadecadien-1-ol and its (E,Z)-isomer. Acetylation of the desired alcohols afford the final products, (Z,Z)-3,13-octadecadien-1-yl acetate(1) and its (E,Z)-isomer(2).

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  1. ChemInform Abstract: A Stereoselective Synthesis of (Z,Z)‐3,13‐Octadecadien‐1‐yl Acetate, and Its (E,Z)‐Isomer, the Sex Pheromone of the Cherry Tree Borer, Synanthedon he vol.20, pp.1, 1988, https://doi.org/10.1002/chin.198901287
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  3. Identification of (Z)-4- and 1-Tridecene in the Metathoracic Gland Secretions of Stink Bugs Employing the GC/FT-IR Technique vol.39, pp.9, 1988, https://doi.org/10.1007/s10886-013-0336-6