Divergent synthesis of four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid, esters and evaluation for the antifungal activity

作者：Wang, Weiwei; Zhang, Xiaoteng; Zhao, Yu; Liu, Xinlei; Zhang, Zhenhua; Wang, Ming'an^*

来源：Chinese Chemical Letters, 2018, 29(12): 1872-1874.

DOI：10.1016/j.cclet.2018.02.006

• 6,7-Dihydroxy-3,7-dimethyloct-2-enoic acid
• Sharpless asymmetry dihydroxylation
• Antifungal activity

The four isomers of 6,7-dihydroxy-3,7-dimethyloct-2-enoic acid 2 were synthesized via the selective direct Sharpless asymmetry dihydroxylation of geraniol as the key step in 35.0%-48.0% overall yields with 91.9%-97.7% ee values for esters 4 and 31.3%-36.4% overall yields with 90.3-97.5% ee values for acids 2 using cis- and trans-geraniol as raw materials. Their structures were characterized by H-1, C-13 NMR and HR-ESI-MS data. The in vivo bioassay results showed that the chiral acid (Z, S)-2 was a good lead compound with 80%-100% inhibitory rates against P. cubensis, E. graminis, P. sorghi and C. gloeosporioides at the concentration of 400 mu g/mL.

• 出版日期2018-12
• 单位中国农业大学