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(S)-(-)-norlaudanosine和(S)-(-)-O,O-dimethylcoclaurine的合成
Synthesis of (S)-(-)-norlaudanosine and (S)-(-)-O,O-dimethylcoclaurine
【摘要】 以高藜芦胺为起始原料,经N-磺酰化反应制得高藜芦磺酰胺(2);2分别与芳乙烯甲醚经对甲苯磺酸催化的Pictet-Spengler反应后用金属钠脱除Ts基团合成了(±)-norlaudanosine(5a)和(±)-O,O-dimethylcoclaurine(5b);使用半量拆分法,以N-乙酰-L-苯丙氨酸为拆分剂,制得(S)-(-)-5a和(S)-(-)-5b,其结构经1H NMR,13C NMR,IR,MS和HR-ESI-MS确证。
【Abstract】 N-Ts homoveratrylamine(2) was prepared by N-sulfonylation of 3,4-diemthoxydopamine.( ±)-Norlaudanosine(5a) and( ±)-O,O-dimethylcoclaurine(5b) were synthesized by Pictet-Spengler reaction of 2 with styryl methyl ethers catalyzed by PTS and removal of Ts group.( S)-(-)-5a and(S)-(-)-5b were obtained by half-equivalent resolution with N-Ac-L-phe. The structures were confirmed by1 H NMR,13 C NMR,IR,MS and HR-ESI-MS.
【关键词】 Pictet-Spengler反应;
norlaudanosine;
O,O-dimethylcoclaurine;
合成;
拆分;
【Key words】 Pictet-Spengler reaction; norlaudanosine; O,O-dimethylcoclaurine; synthesis; resolution;
【Key words】 Pictet-Spengler reaction; norlaudanosine; O,O-dimethylcoclaurine; synthesis; resolution;
【基金】 国家自然科学基金资助项目(20972048);上海市教育发展基金资助项目(03SG27)
- 【文献出处】 合成化学 ,Chinese Journal of Synthetic Chemistry , 编辑部邮箱 ,2014年05期
- 【分类号】O626.323
- 【下载频次】40