3,7-二甲基-7-羟基-2-辛烯-6-内酯类似物的合成及杀菌活性

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

以环氧化-内酯化和Sharpless不对称双羟基化反应作为关键步骤,以55%~90%的总收率实现了消旋及光活性3,7-二甲基-7-羟基-2-辛烯-6-内酯类似物的合成.它们的结构经过^(1)H NMR,^(13)C NMR,HR-ESI-MS和X射线衍射的表征.对它们的杀菌活性进行了评价,结果表明活性最好的化合物3-苯基-7-甲基-7-羟基-2-辛烯-6-内酯(4)和3-(呋喃-2-基)-7-甲基-7-羟基-2-辛烯-6-内酯(5)对6种植物病原菌的EC_(50)值为0.5-20.0μg/mL,可以作为先导结构进行进一步结构优化.

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 ^(1)H NMR,^(13)C NMR,HRMS data,and X-ray diffraction analysis.Their antifungal activities were evaluated,and showed that the EC_(50) values 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 0.5-20.0μg/mL against the tested six phytopathgens,and they were the lead structures to be optimized.