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Pheromones of Coleoptera

13. Synthesis of racemic ferrulactone II from three easily accessible acetylenic precursors

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

Abstract

A ten-step synthesis of a racemic form of 3(Z),1l (S)-dodecen-11-olide (ferrulactone II) has been developed. The synthesis is based on the Cadiot-Chodkiewicz cross-coupling of 4-pentyn-2-ol with 2-propyn-1-ol followed by carbon chain elongation by 3-butyn-1-ol and gives the target lactone in 9.7 % overall yield (based on the starting pentynol). All of the three building blocks used for the chain assembly are easily accessible from acetylene. The protection of OH groups astert-butyl ethers has certain synthetic advantages.

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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. Mavrov & E. P. Serebryakov

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  1. M. V. Mavrov
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  2. E. P. Serebryakov
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Additional information

For part 12, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2122–2125, December, 1993.

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Mavrov, M.V., Serebryakov, E.P. Pheromones of Coleoptera. Russ Chem Bull 42, 2035–2038 (1993). https://doi.org/10.1007/BF00698893

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