Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1458-1461.DOI: 10.6023/cjoc201401021 Previous Articles     Next Articles



杨晓梅a, 张玉顺b, 姚赟b, 陶云海b   

  1. a 云南中医学院中药学院 昆明 650500;
    b 云南大学化学科学与工程学院 昆明 650091
  • 收稿日期:2014-01-13 修回日期:2014-03-16 发布日期:2014-04-01
  • 通讯作者: 陶云海
  • 基金资助:


Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth

Yang Xiaomeia, Zhang Yushunb, Yao Yunb, Tao Yunhaib   

  1. a School of Traditional Chinese Medicine, Yunnan University of Traditional Chinese Medicine, Kunming 650500;
    b School of Chemistry Science and Engineering, Yunnan University, Kunming 650091
  • Received:2014-01-13 Revised:2014-03-16 Published:2014-04-01
  • Supported by:

    Project supported by the Science and Technology Foundation of Yunnan University (No. 2011YB12) and the Foundation of Yunnan Province Department of Education (No. 2011Y112).

Peach fruit moth is one of the most serious pests, whose sex pheromone is (Z)-7-eicosen-11-one. Synthesis of the compound was achieved from 2,3-dihydrofuran. Firstly, acidic hydrolysis of 2,3-dihydrofuran gave 4-hydroxybutanal, which reacted with the ylide prepared from heptyltriphenylphosphonium bromide to afford (Z)-4-undecen-1-ol. The alcohol was oxidated followed by Grignard addition and further oxidation to give the target product.

Key words: carposina sasakii matsumura, (Z)-7-eicosen-11-one, pheromone synthesis, Wittig reaction, Grignard addition