文献类型：期刊文献

英文题名：Improved Stereoselective Syntheses of (+)-Valiolamine and (+)-Valienamine Starting from (-)-Shikimic Acid

作者：Li, Fenglei[1];Ding, Wei[1];Quan, Na[1];Wu, Jiajia[1];He, Yungang[1];Zhu, Xingliang[1];Shi, Xiaoxin[1];Zhao, Jianhong[1]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

年份：2017

卷号：35

期号：4

起止页码：457

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000399971900014)，CCR-EXPANDED(收录号:WOS:000399971900014)】；

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

语种：英文

外文关键词：valiolamine; valienamine; shikimic acid; practical synthesis

摘要：Improved stereoselective syntheses of the target compounds (+)-valiolamine 1 and (+)-valienamine 2 starting from naturally abundant (-)-shikimic acid are described. A common key intermediate compound 7 was first synthesized from (-)-shikimic acid in 9 steps. The compound 7 was then converted to (+)-valiolamine 1 in 3 steps, and was also converted to (+)-valienamine 2 in 4 steps. In summary, (+)-valiolamine 1 and (+)-valienamine 2 were synthesized from (-)-shikimic acid in 12 (or 13) steps in 40% and 39% overall yields, respectively. The present syntheses are more practical and might be important for the potential industrial preparations of pharmaceutically valuable (+)-valiolamine 1 and (+)-valienamine 2.