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A novel polyfunctional chiral building block derived from (S)-ethyl lactate. Application to the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi)

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

Abstract

Highly enantiomerically pure (4S, 5E)-4-bromomethylhept-5-enenitrile was prepared from (S)-ethyl lactate by a six-step procedure involving a rearrangement of chiral cyclopropylcarbinol. This product was used for the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi), (10R)-10-methyltridecan-2-one.

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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

    M. V. Zlokazov & V. V. Veselovsky

Authors
  1. M. V. Zlokazov
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  2. V. V. Veselovsky
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Additional information

For preliminary communication, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 151–155, January, 2000.

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Zlokazov, M.V., Veselovsky, V.V. A novel polyfunctional chiral building block derived from (S)-ethyl lactate. Application to the synthesis of the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata howardi). Russ Chem Bull 49, 154–158 (2000). https://doi.org/10.1007/BF02499083

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  • DOI: https://doi.org/10.1007/BF02499083

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