文献类型：期刊文献

英文题名：A novel stereoselective synthesis of (-)-quinic acid starting from the naturally abundant (-)-shildmic acid

作者：Zhang, Wei[2];Zhu, Xing-Liang[2];Ding, Wei[2];Shi, Xiao-Xin[1,2]

机构：[1]E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Engn, Shanghai 200237, Peoples R China

年份：2015

卷号：26

期号：23

起止页码：1375

外文期刊名：TETRAHEDRON-ASYMMETRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000366070000010)，CCR-EXPANDED(收录号:WOS:000366070000010)】；

基金：We are grateful to the National Natural Science Foundation of China (No. 20972048) for the financial support of this work.

语种：英文

摘要：A new stereoselective synthesis of (-)-quinic acid from the naturally abundant (-)-shildmic acid is described. Ethyl shikimate 2 was first prepared in 97% yield via esterification of (-)-shildmic acid according to a previous report. Ester 2 was then transformed into an epimeric mixture of 3,4-O-benzylidene shikimate 3, which was directly converted into compound 4 in 90% yield (over 2 steps from ester 2) via an NBS-mediated acetal ring-opening reaction. Acetylization of the hydroxyl group at the C-5 position of compound 4 gave compound 5 in 98% yield. Compound 5 was transformed into compound 6 in 91% yield via a highly stereoselective Ru-catalyzed dihydroxylation. Subsequently, compound 6 was converted into epoxide 7 in 82% yield via an intramolecular S(N)2 type substitution. A regioselective epoxide-opening of compound 7 by PPh3-I-2 complex furnished an iodo compound 8 in 79% yield. Removal of the iodine atom in compound 8 by Pd/C-catalyzed hydrogenation produced compound 9 in 92% yield. Methanolysis of compound 9 gave methyl quinate 10 in 92% yield. Finally, hydrolysis of compound 10 afforded the targeted compound (-)-quinic acid 1 in 90% yield. The title compound (-)-quinic acid I was stereoselectively synthesized through 10 steps starting from (-)-shildmic acid in 38% overall yield. (C) 2015 Elsevier Ltd. All rights reserved.