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Terpenes in organic synthesis. Communication 1. Synthesis of (1R, 3S)-1-acetoxymethyl-3-isopropenyl-2,2-dimethylcyclobutane (sex pheromone of the grape mealybug) from verboxide

  • E. P. Serebryakov
  • L. M. Suslova
  • A. M. Moiseenkov
  • S. V. Shavyrin
  • N. V. Zaikina
  • A. M. Sorochinskaya
  • B. G. Kovalev
Organic Chemistry
  • 25 Downloads

Conclusions

  1. 1.

    (1R, 3S)-l-Acetoxymethyl-3-isopropenyl-2,2-dimethylcyclobutane, a sex attractant of the grape mealy bugPlanococcus citri (Risso), was synthesized in five steps from technical grade verboxide.

     
  2. 2.

    The overall yield of pheromone from verboxide is 2.2–2.5%, while its optical purity (43–70%) correlates with the optical purity of α-pinene converted into verboxide.

     

Keywords

Terpene Organic Synthesis Technical Grade Optical Purity Dimethylcyclobutane 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • E. P. Serebryakov
    • 1
    • 2
    • 3
  • L. M. Suslova
    • 1
    • 2
    • 3
  • A. M. Moiseenkov
    • 1
    • 2
    • 3
  • S. V. Shavyrin
    • 1
    • 2
    • 3
  • N. V. Zaikina
    • 1
    • 2
    • 3
  • A. M. Sorochinskaya
    • 1
    • 2
    • 3
  • B. G. Kovalev
    • 1
    • 2
    • 3
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow
  2. 2.Scientific-Research and Planning Institute of Wood Chemical IndustryGorkii
  3. 3.All-Union Scientific-Research Institute of Biological Methods of Plant ProtectionKishinev

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