Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 301-308.DOI: 10.6023/cjoc202305023 Previous Articles     Next Articles



于士航, 刘嘉威, 安碧玉, 边庆花*(), 王敏, 钟江春*()   

  1. 中国农业大学理学院 应用化学系 北京 100193
  • 收稿日期:2023-05-17 修回日期:2023-06-24 发布日期:2023-07-19
  • 作者简介:
  • 基金资助:

Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius)

Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian(), Min Wang, Jiangchun Zhong()   

  1. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193
  • Received:2023-05-17 Revised:2023-06-24 Published:2023-07-19
  • Contact: *E-mail:; E-mail:
  • About author:
    These authors contributed equally to this work.
  • Supported by:
    National Key Research and Development Program of China(2017YFD0201404)

Neoclytus acuminatus acuminatus (Fabricius) is a wood-boring pest of forests and orchards. Its contact sex pheromones were (R)-9-methylheptacosane, (R)-7-methylheptacosane and (R)-7-methylpentacosane. A new and efficient synthesis of the contact sex pheromone was developed from chiral synthon of (S)-2-methyloxirane. This procedure mainly involved ring-opening reaction of (S)-2-methyloxirane, SN2 allylation of secondary tosylate and Wittig coupling of chiral aldehyde.

Key words: Neoclytus acuminatus acuminatus, contact sex pheromone, chiral source, (S)-2-methyloxirane, asymmetric synthesis