Citation: Wang Weiwei, Zhang Xiaoteng, Zhao Yu, Liu Xinlei, Zhang Zhenhua, Wang Ming'an. Divergent synthesis of four isomers of 6, 7-dihydroxy-3, 7-dimethyloct-2-enoic acid, esters and evaluation for the antifungal activity[J]. Chinese Chemical Letters, ;2018, 29(12): 1872-1874. doi: 10.1016/j.cclet.2018.02.006 shu

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

Department of Applied Chemistry, China Agricultural University, Beijing 100193, China

wangma@cau.edu.cn

Received Date: 30 December 2017
Revised Date: 30 January 2018
Accepted Date: 10 February 2018
Available Online: 15 December 2018

Figures(5)

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 ¹H, ¹³C 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 μg/mL.
- 6, 7-Dihydroxy-3, 7-dimethyloct-2-enoic acid,
- Sharpless asymmetry dihydroxylation,
- Antifungal activity
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