Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of (Z)-, and (E)-8-Dodecen-1-yl Acetate, The Sex Pheromone of the Oriental Fruit Moth, Grapholitha Molesta by Stereochemical Control in Wittig Olefination

  • Kang, Suk-Ku (Department of Chemistry, Sung Kyun Kwan University Natural Science Campus) ;
  • Kim, Jung-Hawn (Department of Chemistry, Sung Kyun Kwan University Natural Science Campus) ;
  • Shin, Yaung-Chul (Department of Chemistry, Sung Kyun Kwan University Natural Science Campus)
  • Published : 1986.12.20
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Abstract

Stereochemical control of the Wittig reaction of the primary aldehyde, 8-acetoxyoctan-1-al (7) with the nonstabilized alkylide, triphenylphosphonium n-butylide (6), was achieved by controlling the reaction conditions including solvent, temperature and inorganic salts. These conditions can be applied to the direct sythesis of the mixture of (Z)-, and (E)-8-dodecen-1-yl acetate, the sex pheromone of the oriental fruit moth, Grapholitha molesta. The primary aldehyde, 8-acetoxyoctan-1-al (7) was synthesized from 1,8-octanediol which is cheap and readily available.

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Cited by

  1. ChemInform Abstract: Synthesis of (Z)‐, and (E)‐8‐Dodecen‐1‐yl Acetate, the Sex Pheromone of the Oriental Fruit Moth, Grapholitha molesta by Stereochemical Control in Wit vol.18, pp.27, 1986, https://doi.org/10.1002/chin.198727320
  2. Cis-1,8-dibromo-4-octene을 이용한 복숭아순나방(Grapholita molesta)성 페로몬의 입체특이적 합성 vol.52, pp.5, 1986, https://doi.org/10.5012/jkcs.2008.52.5.588
  3. A facile synthesis of the sex pheromone of Grapholitha molesta vol.48, pp.1, 2012, https://doi.org/10.1007/s10600-012-0168-6