Synthesis of the Deuterated Sex Pheromone Components of the Grape Borer,<i>Xylotrechus pyrrhoderus</i>

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  • KIYOTA Ryutaro
    Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology
  • YAMAKAWA Rei
    Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology
  • IWABUCHI Kikuo
    Department of Applied Biological Science, Faculty of Agriculture, Tokyo University of Agriculture and Technology
  • HOSHINO Keita
    Department of Applied Biological Science, Faculty of Agriculture, Tokyo University of Agriculture and Technology
  • ANDO Tetsu
    Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology

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  • Synthesis of the Deuterated Sex Pheromone Components of the Grape Borer, Xylotrechus pyrrhoderus

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Adult males of the grape borer, Xylotrechus pyrrhoderus, secrete (S)-2-hydroxy-3-octanone [(S)-1] and (2S,3S)-2,3-octanediol [(2S,3S)-2] from their nota of prothoraces as sex pheromone components. Their structural similarity suggests that one of them is the biosynthetic precursor of the other component. In order to confirm the biochemical conversion, deuterated derivatives of both components were synthesized by starting from a Wittig reaction between hexanal and an ylide derived from D5-iodoethane and ending with enantiomeric resolution by chiral HPLC. The molecular ions of 1 and 2 could scarcely be detected by using a GC-MS analysis, and the labeled compounds showed similar mass spectra to the unlabeled pheromone components. However, several fragment ions, including four deuterium atoms, were observed in the mass spectra of their acetate derivatives, indicating that the conversion could be confirmed by examining a compound with the diagnostic ions after acetylation of the volatiles collected from insects treated with the labeled precursors.

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