DOI QR코드

DOI QR Code

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

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).

Keywords

References

  1. Appl. Ent. Zool. v.11 no.3 K. Yaginuma;Y. Tamaki;T. Yushima;J. H. Tumlinson
  2. Ent. Exp. Appl. v.23 no.3 S. Voerman;A. K. Minks;G. Vanwetswinkel;J. H Tumlinson
  3. Insect Sex Pheromone Korea Advanced Institute of Science and Technology
  4. Bull. Fukushima Horticult. Exp. Stn v.1 M. Kumakura;K. Yaginuma;M. Suzaki
  5. Science v.185 J. H. Tumlinson;C. E. Younce;R. E. Doolittle;R. R. Heath;C. R. Gentry;E. R. Mitctell
  6. Research Report on the Utilization of Sex Pheromones Y. Tamaki;T. Yushima;M. Oda;K. Kida;K. Kitamura;T. Yabuki;J. H. Tumlinson
  7. Agric. Biol. Chem. v.42 M. Uchida;K. Mori;M. Matsui
  8. Agric. Biol. Chem. v.43 T. Ebata;K. Mori
  9. Agric. Biol. Chem. v.43 M. Uchida, K. Nakagawa;K. Mori
  10. J. Chem. Ecol. v.5 S. Voerman
  11. J. Chem. Ecol. v.9 M. Gardette;A. Alexakis;J. F. Normant
  12. Tetrahedron Letters P. Vinczer;G. Baan;L. Novak;C. Szantay
  13. Synthesis S-K. Kang;W-S. Kim;B-H. Moon
  14. J. Org. Chem. v.42 N. Miyashita;A. Yoshikoshi;P. A. Grieco
  15. J. Am. Chem., Soc. v.78 D. J. Cram;N. C. Allinger
  16. Tetrahedron Letters E. J. Corey;J. W. Suggs
  17. Helv. Chim. Acta. v.64 E-P. Krebs
  18. J. Org. Chem. v.47 A. S. Kende;B. H. Toder
  19. Tetrahedron Letters Y. Ikeda;H. Yamamoto
  20. Tetrahedron Y. Ikeda;J. Ukai;N. Ikeda;H. Yamamoto

Cited by

  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
  2. Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis vol.33, pp.3, 1988, https://doi.org/10.1007/s10886-006-9246-1
  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