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Synthesis of 7E,9Z-dodecadienyl acetate, the sex pheromone ofLobesia botrana Shiff

  • Chemistry of Natural Compounds and Bioorganic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Two syntheses of 7E,9Z-dodecadienyl acetate from 1,3-butadiyne were carried out using either 2E,4Z-heptadienyl acetate or 1-bromo-3E,5Z-octadiene as the key intermediates. The latter underwent organocopper cross-coupling with the respective complementary Grignard reagents (prepared from the corresponding 1-tert-butoxy-ω-chlorohydrins) as alkylating agents.

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Authors and Affiliations

  1. P. G. Melikishvili Institute of Physical and Organic Chemistry, Georgian Academy of Sciences, 380086, Tbilisi, Georgia

    Z. G. Chrelashvili & A. V. Dolidze

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    M. V. Mavrov & E. P. Serebryakov

  3. State Research and Designing Institute of the Methanol Industry (GOSNIIMETANOLPROEKT), 344940, Severodonetsk, Ukraine

    A. P. Voronkov

Authors
  1. Z. G. Chrelashvili
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  2. M. V. Mavrov
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  3. A. V. Dolidze
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  4. A. P. Voronkov
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  5. E. P. Serebryakov
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Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 766–768, April, 1993.

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Chrelashvili, Z.G., Mavrov, M.V., Dolidze, A.V. et al. Synthesis of 7E,9Z-dodecadienyl acetate, the sex pheromone ofLobesia botrana Shiff. Russ Chem Bull 42, 734–736 (1993). https://doi.org/10.1007/BF00704016

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  • DOI: https://doi.org/10.1007/BF00704016

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