Chinese Journal of Organic Chemistry >
Synthesis and Antifungal Activity of 3-Aryl-7-methyl- 7-hydroxy-2-octen-6-olide
Received date: 2021-01-28
Revised date: 2021-02-24
Online published: 2021-03-22
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.
Weiwei Wang , Yu Zhao , Xinlei Liu , Jiazhen Jiang , Ming'an Wang . Synthesis and Antifungal Activity of 3-Aryl-7-methyl- 7-hydroxy-2-octen-6-olide[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2343 -2353 . DOI: 10.6023/cjoc202101049
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