天然产物E/Z-Isoaurostatin的选择性合成  

Geometrical Selective Synthesis of E/Z-Isoaurostatin

作　　者：魏文[1] 徐田龙[1] 罗翔 宋现恒 邹永[2] WEI Wen;XU Tian-long;LUO Xiang;SONG Xian-heng;ZOU Yong(Guangzhou Chemical Co.,LTD,Chinese Academy of Sciences,Guangzhou 510650,China;School of Pharmaceutical Sciences,Sun Yat-Sen Univerisity,Guangzhou 510006,China)

机构地区：[1]中科院广州化学有限公司,广东广州510650 [2]中山大学药学院,广东广州510006

出　　处：《广州化学》2019年第4期1-6,共6页Guangzhou Chemistry

基　　金：国家重点研发计划项目（2016YFA0602900）;广东省自然科学基金项目（2016A030311033）;广州市科技计划项目（201505041557046）

摘　　要：以间溴苯酚为起始物,经与一水合乙醛酸的亲核加成反应得到2-溴-4-羟基扁桃酸(2),经还原反应得到2-溴-4-羟基苯乙酸(3),再与对羟基苯甲醛(4)经Perkin反应制备得到E-2-(2-溴-4-羟基苯基)-3-(4-羟基苯基)丙烯酸(5)。最后,分别在Cu2O/Na2CO3/DMF或Cu2O/1,10-phen/PEG-400的条件下选择性制备得到E或Z-3-(4’-羟基)苯亚甲基-6-羟基苯并呋喃-2-酮(6a,6b)。Starting from 3-bromophenol,the nucleophilic addition reaction with glyoxylic acid monohydrate provided 2-bromo-4-hydroxymandelic acid,which was further transformed by reduction to give 2-bromo-4-hydroxyphenylacetic acid.Perkin reaction between 2-bromo-4-hydroxyphenylacetic acid and p-hydroxy-benzaldehyde afforded E-2-(2-bromo-4-hydroxyphenyl)-3-(4-hydroxyphenyl)acrylic acid.Finally,under the reaction conditions of Cu2O/Na2CO3/DMF or Cu2O/1,10-phen/PEG-400/MW,the desired products E-Isoaurostatin(6a)and Z-Isoaurostatin(6b)could be obtained respectively.Protection and deprotection were not needed in this protocol,and the use of toxic,hazardous,irritanting and corrosive reagents and solvents were abandoned.Atom-and step-economic synthetic route,ease of operation,eco-friendliness,and high yields were the notable features of this strategy.

关 键 词：Isoaurostatin E-式和Z-式 天然产物 合成 

分 类 号：O629.6[理学—有机化学]