Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1646-1657.DOI: 10.6023/cjoc202010011 Previous Articles     Next Articles



董宏波1, 王卫伟1, 赵宇1, 刘鑫磊1, 王明安1,*()   

  1. 1 中国农业大学应用化学系 农药创新研究中心 北京 100193
  • 收稿日期:2020-10-09 修回日期:2020-11-20 发布日期:2020-12-19
  • 通讯作者: 王明安
  • 基金资助:
    国家自然科学基金(21772229); 国家自然科学基金(21172254)

Synthesis and Antifungal Activity of 3,7-Dimethyl-7-hydroxy-2-octen-6-olide Analogues

Hongbo Dong1, Weiwei Wang1, Yu Zhao1, Xinlei Liu1, Ming'an Wang1,*()   

  1. 1 Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2020-10-09 Revised:2020-11-20 Published:2020-12-19
  • Contact: Ming'an Wang
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    National Natural Science Foundation of China(21772229); National Natural Science Foundation of China(21172254)

The synthesis of racemic and optical 3,7-dimethyl-7-hydroxy-2-octen-6-olide analogues has been achieved via epoxidation-lactonization procedure and Sharpless asymmetric dihydroxylation as the key steps in 55%~90% overall yields, respectively. Their structures were fully characterized by 1H NMR, 13C NMR, HRMS data, and X-ray diffraction analysis. Their antifungal activities were evaluated, and showed that the EC50values of the most active compounds 3-phenyl-7- methyl-7-hydroxy-2-octen-6-olide (4) and 3-(furan-2-yl)-7-methyl-7-hydroxy-2-octen-6-olide (5) were in the range of 0.5~20.0 μg/mL against the tested six phytopathgens, and they were the lead structures to be optimized.

Key words: 3,7-dimethyl-7-hydroxy-2-octen-6-olide, epoxidation-lactonization, asymmetric dihydroxylation, antifungal activity