文献类型：期刊文献

中文题名：Efficient and Practical Syntheses of Enantiomerically Pure (S)-(?)-Norcryptostyline Ⅰ, (S)-(?)-Norcryptostyline Ⅱ, (R)-(+)-Salsolidine and (S)-(?)-Norlaudanosine via a Resolution-Racemization Method

作者：Ruiheng Zhu[1];Zhangli Xu[1];Wei Ding[1];Shiling Liu[1];Xiaoxin Shi[1];Xia Lu[1]

机构：[1]Department of Pharmaceutical Engineering,School of Pharmacy,East China University of Science and Technology,130 Mei-Long Road,Shanghai 200237,China

年份：2014

卷号：32

期号：10

起止页码：1039

中文期刊名：Chinese Journal of Chemistry

外文期刊名：中国化学（英文版）

收录：CSTPCD;;Scopus;CSCD:【CSCD2013_2014】；PubMed;

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

语种：英文

中文关键词：tetrahydroisoquinolines;norcryptostyline;salsolidine;norlaudanosine;resolution;racemization

摘要：Four racemic tetrahydroisoquinolines(RS)-(±)-1-4 were prepared from homoveratrylamine via amidation,Bischler-Napieralski reaction and the subsequent reduction.The enantiomerically pure tetrahydroisoquinolines(S)-(?)-norcryptostyline Ⅰ[(S)-(?)-1],(S)-(?)-norcryptostyline Ⅱ[(S)-(?)-2],(R)-(+)-salsolidine[(R)-(+)-3]and(S)-(?)-norlaudanosine[(S)-(?)-4]were then obtained in 45%,40%,41%and 38%yields,respectively,via resolution of the racemic compounds(RS)-(±)-1-4 with half equivalent of chiral acids.In addition,the enantiomerically enriched compounds(R)-(+)-1,(R)-(+)-2,(S)-(?)-3 and(R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.