Chinese Journal of Organic Chemistry >
Synthesis and Antifungal Activity of 3,7-Dimethyl-7-hydroxy-2-octen-6-olide Analogues
Received date: 2020-10-09
Revised date: 2020-11-20
Online published: 2020-12-19
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.
Hongbo Dong , Weiwei Wang , Yu Zhao , Xinlei Liu , Ming'an Wang . Synthesis and Antifungal Activity of 3,7-Dimethyl-7-hydroxy-2-octen-6-olide Analogues[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1646 -1657 . DOI: 10.6023/cjoc202010011
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