(S)-(-)-norlaudanosine和(S)-(-)-O,O-dimethylcoclaurine的合成

Synthesis of (S)-(-)-norlaudanosine and (S)-(-)-O,O-dimethylcoclaurine

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。

A N-Ts homoveratrylamine （2） was prepared by N-sulfonylation of 3,4-diemthoxydopamine. （ ± ） -Norlaudanosine（5a） and （ ± ） -O, O-dimethyleoelaurine （5b） were synthesized by Pietet - Spengler reaction of 2 with styryl methyl ethers catalyzed by ITS and removal of Ts group. （S） - （ - ）-5a and （S）-（ - ）-5b were obtained by half-equivalent resolution with N-Ae-L-phe. The struc- tures were confirmed by 1H NMR, 13C NMR, IR, MS and HR-ESI-MS.