Molecules (Jun 2024)

Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, <i>Lyclene dharma dharma</i>, and Their Enantiomers

  • Yun Zhou,
  • Jianan Wang,
  • Yueru Zhang,
  • Xiaochen Fu,
  • Hongqing Xie,
  • Jinlong Han,
  • Jianhua Zhang,
  • Jiangchun Zhong,
  • Chenggang Shan

DOI
https://doi.org/10.3390/molecules29122918
Journal volume & issue
Vol. 29, no. 12
p. 2918

Abstract

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The Lichen moth, Lyclene dharma dharma (Arctiidae, Lithosiinae), plays a significant role in forest ecosystem dynamics. A concise and novel method to synthesize the active sex pheromone components, (S)-14-methyloctadecan-2-one ((S)-1), (S)-6-methyloctadecan-2-one ((S)-2), and their enantiomers has been developed. Key steps in the synthesis include the use of Evans’ chiral auxiliaries, Grignard cross-coupling reactions, hydroboration–oxidation, and Wacker oxidation. The synthesized sex pheromone components hold potential value for studies on communication mechanisms, species identification, and ecological management.

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