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Synthesis of 3(Z)-dodecen-12-olide—an aggregation pheromone of the flat grain beetleCryptolestes pusillus (Coleoptera:Cucujidae)

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

Abstract

3(Z)-Dodecen-12-olide, an aggregation pheromone of the flat grain beetle, was obtained using 1,4-cis-hydrogenation of ethyl 12-hydroxydodeca-2,4-dienoate as a key step. The dienoic ester was synthesized from 10-hydroxydec-2-enal, which, in turn, was prepared from its saturated precursorvia acetal α-bromination followed by phenylselenation/oxidative elimination/hydrolysis.

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Authors and Affiliations

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

    A. A. Vasil'ev & V. M. Merkulova

  2. Institute of Chemistry, Department of Organic Chemistry, Uppsala University, Box 531, 751 21, Uppsala, Sweden

    L. Engman

Authors
  1. A. A. Vasil'ev
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  2. L. Engman
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  3. V. M. Merkulova
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Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1300–1303, July, 2000.

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Vasil'ev, A.A., Engman, L. & Merkulova, V.M. Synthesis of 3(Z)-dodecen-12-olide—an aggregation pheromone of the flat grain beetleCryptolestes pusillus (Coleoptera:Cucujidae). Russ Chem Bull 49, 1297–1300 (2000). https://doi.org/10.1007/BF02495778

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  • DOI: https://doi.org/10.1007/BF02495778

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