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

作     者：Weiwei Wang Xiaoteng Zhang Yu Zhao Xinlei Liu Zhenhua Zhang Ming'an Wang 

作者机构：Department of Applied Chemistry China Agricultural University 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2018年第29卷第12期

页      面：1872-1874页

核心收录：

学科分类：1007[医学-药学(可授医学、理学学位)] 100705[医学-微生物与生化药学] 10[医学] 

基　　金：the National Natural Science Foundation of China(Nos.21772229 21172254)for the financial support 

主　　题：6,7-Dihydroxy-3,7-dimethyloct-2-enoic acid Sharpless asymmetry dihydroxylation Antifungal activity 

摘      要：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 with91.9%-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,;C 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.