手性嘧啶核苷的不对称合成（英文）

【作者】 王海霞； 王东超； 谢明胜； 渠桂荣； 郭海明；

【机构】 河南师范大学化学化工学院；

【摘要】 Pyrimidine nucleosides have displayed important antivirus activities with versatile applications in medicinal chemistry,and representative examples shown in Figure 1.Especially,Azvudine （FNC） is being investigated in phase II clinical trial for the treatment of HIV.However,resistances are emerging in viral infections and new viruses are appearing.Therefore,developing an efficient method to construct new chiral pyrimidine nucleosides is highly desirable.In this work,we developed an efficient method to construct chiral pyrimidine-substituted diester D-A cyclopropanes via enantioselective cyclopropanation of N1-vinylpyrimidines with phenyliodonium ylides.^1-4 With the Cu（OTf）₂-L5 as the catalyst,diverse N1-vinylpyrimidines worked well,generating chiral pyrimidine-substituted diester D-A cyclopropanes in up to 97%yield and up to 99%ee （Figure 2）.Through simple[3+2]annulation of chiral cyclopropanes with benzaldehyde or ethyl glyoxylate,different chiral pyrimidine nucleoside analogues with a sugar ring could be obtained.更多还原

【Abstract】 Pyrimidine nucleosides have displayed important antivirus activities with versatile applications in medicinal chemistry,and representative examples shown in Figure 1.Especially,Azvudine （FNC） is being investigated in phase II clinical trial for the treatment of HIV.However,resistances are emerging in viral infections and new viruses are appearing.Therefore,developing an efficient method to construct new chiral pyrimidine nucleosides is highly desirable.In this work,we developed an efficient method to construct chiral pyrimidine-substituted diester D-A cyclopropanes via enantioselective cyclopropanation of N1-vinylpyrimidines with phenyliodonium ylides.^1-4 With the Cu（OTf）₂-L5 as the catalyst,diverse N1-vinylpyrimidines worked well,generating chiral pyrimidine-substituted diester D-A cyclopropanes in up to 97%yield and up to 99%ee （Figure 2）.Through simple[3+2]annulation of chiral cyclopropanes with benzaldehyde or ethyl glyoxylate,different chiral pyrimidine nucleoside analogues with a sugar ring could be obtained.更多还原