Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2343-2353.DOI: 10.6023/cjoc202101049 Previous Articles     Next Articles



王卫伟(), 赵宇, 刘鑫磊, 蒋家珍, 王明安*   

  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:2021-01-28 修回日期:2021-02-24 发布日期:2021-03-22
  • 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); 国家高科技研发计划(2011AA10A202)

Synthesis and Antifungal Activity of 3-Aryl-7-methyl- 7-hydroxy-2-octen-6-olide

Weiwei Wang(), Yu Zhao, Xinlei Liu, Jiazhen Jiang, Ming'an Wang   

  1. Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2021-01-28 Revised:2021-02-24 Published:2021-03-22
  • Contact: Ming'an Wang
  • Supported by:
    National Natural Science Foundation of China(21772229); National Natural Science Foundation of China(21172254); National Hi-Tech R & D Program of China(2011AA10A202)

In order to optimize the structure of 3-phenyl-7-methyl-7-hydroxy-2-octen-6-olide, the synthesis of racemic and optical 3-aryl-7-methyl-7-hydroxy-2-octen-6-olides has been achieved via epoxidation-lactonization procedure and Sharpless asymmetric dihydroxylation as the key steps in 61%~91% yields, respectively. Their structures were fully characterized by IR, 1H NMR, 13C NMR, and HRMS data. Their antifungal activities were evaluated, and it showed that (R)-3-phenyl-7-methyl- 7-hydroxy-2-octen-6-olide (5a) was the most active compound with the EC 50 values in the range of 0.2~13.5 µg/mL against the tested six phytopathogens, better than its ( S)-isomer and racemic mixture. It would be the potential lead structure to be optimized. The scanning electron microscopy (SEM) and transmission electron microscopy (TEM) observation indicated that compounds (S)-5a, 5d and 5j had a significant impact on the structure and function of the hyphal cell wall of S. sclerotiorum mycelium.

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