Synthesis of (4R,9Z)‐9‐Octadecen‐4‐olide, the Female Sex Pheromone of Janus integer, and Its Enantiomer

@article{Shibata2004SynthesisO,
  title={Synthesis of (4R,9Z)‐9‐Octadecen‐4‐olide, the Female Sex Pheromone of Janus integer, and Its Enantiomer},
  author={Chi{\'e} Shibata and K. Mori},
  journal={European Journal of Organic Chemistry},
  year={2004},
  volume={2004},
  pages={1083-1088}
}
  • Chié Shibata, K. Mori
  • Published 2004
  • Chemistry
  • European Journal of Organic Chemistry
  • Enantiomer separation of (±)-8-tert-butyldiphenylsilyloxy-1-octyn-3-ol was achieved by lipase-mediated asymmetric acetylation. The resolved (R)-alkynol was converted into (4R,9Z)-9-octadecen-4-olide, which was identical with the female sex pheromone of the currant stem girdler (Janus integer). The absolute configuration of the natural pheromone was thus established as R. (4S,9Z)-9-Octadecen-4-olide was also synthesized, and found to be pheromonally inhibitory. (© Wiley-VCH Verlag GmbH & Co… CONTINUE READING
    10 Citations
    Synthesis of Pheromones: Highlights from 2002-2004
    • 7
    • PDF
    The use of the lactone motif in chemical communication.
    • 37
    • PDF
    Synthesis of Pheromones: Highlights from 2005-2007
    • 5