Chemistry of Natural Compounds

, Volume 22, Issue 5, pp 595–597 | Cite as

Insect pheromones and their analogs. XV. The synthesis of 9-oxodec-2E-enoic acid — A pheromone of the honeybeeApis melliferana

  • V. N. Odinokov
  • G. Yu. Ishmuratov
  • I. M. Ladenkova
  • G. A. Tolstikov
Article

Abstract

A new effective route to the synthesis of 7-oxooctanal has been found which is based on the ozonolysis of the tetrahydropyran-2-yl ether of 7-methyloct-7-en-l-ol — the product of the coupling of the readily available methallyl chloride and the Grignard reagent from the corresponding ether of 5-bromopentan-l-ol. From the 7-oxooctanal has been obtained 9-oxodec-2E-enoic acid — a pheromone of the honeybeeApis melliferana.

Keywords

Diethyl Ether Malonic Acid Grignard Reagent MgBr Hydroxy Ketone 

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Literature cited

  1. 1.
    K. V. Lebedeva, V. A. Minyailo, and Yu. B. Pyatnova, Insect Pheromones [in Russian], Moscow (1984), p. 268.Google Scholar
  2. 2.
    M. Barbier, Helv. Chim. Acta, No. 5,64, 1407 (1981).CrossRefGoogle Scholar
  3. 3.
    Yu. I. Pyatraitis, Khemoretseptsiya Nasekomykh,4, 71 (1979).Google Scholar
  4. 4.
    L. I. Zakharkin and D. A. Kamernitskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 443 (1981).Google Scholar
  5. 5.
    R. N. Majee, R. Ramani, and S. N. Mukherjee, Curr. Sci.52, No. 7, 320 (1983).Google Scholar
  6. 6.
    A. Chattopadhyay, V. R. Mamdapur, and M. S. Chadha, Indian J. Chem.,22, No. 2, 158 (1983).Google Scholar
  7. 7.
    V. Kh. Taksidi, S. G. Lavrenko, L. A. Shkolina, et al., New Chemical Plant-Protection Agents [in Russian], NIITEKhim, Moscow (1979), p. 37.Google Scholar

Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • V. N. Odinokov
  • G. Yu. Ishmuratov
  • I. M. Ladenkova
  • G. A. Tolstikov

There are no affiliations available

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