文献类型：期刊文献

英文题名：Total Syntheses of (+)-Valiolamine and (-)-1-epi-Valiolamine from Naturally Abundant (-)-Shikimic Acid

作者：Quan, Na[1];Nie, Liang-Deng[1];Zhu, Rui-Heng[1];Shi, Xiao-Xin[1];Ding, Wei[1];Lu, Xia[1]

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

年份：2013

卷号：2013

期号：28

起止页码：6389

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000324932400025)，CCR-EXPANDED(收录号:WOS:000324932400025)】；

基金：The authors thank the National Natural Science Foundation of China (NSFC) (grant number 20972048) for financial support of this work.

语种：英文

外文关键词：Total synthesis; Drug design; Natural products; Carbohydrates; Inhibitors

摘要：Total syntheses of (+)-valiolamine (1) and (-)-1-epi-valiolamine (2) from the naturally abundant (-)-shikimic acid are described. Ethyl 3-epi-5-O-methylsulfonyl-shikimate (3), as the key common intermediate, was first synthesized in five steps in 74% overall yield, and then converted into the targets 1 and 2 in seven steps in 48 and 41% overall yield, respectively.