Total Synthesis of Nucleoside Antibiotics Amicetin,Plicacetin,and Cytosaminomycin A-D  

作　　者：Jiqiang Fu Peng Xu Biao Yu 

机构地区：[1]State Key Laboratory of Bioorganic and Natural Products Chemistry,Center for Excellence in Molecular Synthesis,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,345 Lingling Road,Shanghai,200032 China [2]School of Chemistry and Materials Science,Hangzhou Institute for Advanced Study,University of Chinese Academy of Sciences,1 Sub-lane Xiangshan,Hangzhou,Zhejiang,310024 China

出　　处：《Chinese Journal of Chemistry》2021年第10期2679-2684,共6页中国化学（英文版）

基　　金：the National Natural Science Foundation of China(Nos.21861162011,22031011,&21621002);the National Key Research&Development Program of China(No.2018YFA0507602);the Key Research Program of Frontier Sciencesof CAS(No.ZDBS-LY-SLH030);the Strategic Priority Research Program of CAS(No.XDB20020000);the Youth Innovation Promotion Association of CAS(No.2020258)are acknowledged.

摘　　要：Main observation and conclusion Amicetin and congeners constitute a small family of complex pyrimidine nucleosides,which exhibit strong antibiotic activities against Gram-positive bacteria and notably against strains of Mycobacterium tuberculosis.Herein,we report chemical synthesis of a series of disaccharide congeners of the amicetin family,including amicetin,plicacetin,and cytosaminomycin A—D.It is the first time for successful synthesis of amicetin,the prototypical member,and cytosaminomycins.The synthetic approach employs glycosyl N-phenyltrifluoroacetimidate and thioglycoside donors to construct the characteristic aminodeoxydisaccharides consisting ofα-(1→4)-glycosidic linkage,uses gold(I)-catalyzed N-glycosylation to furnish 2-deoxy-β-nucleosides,and finally exploits amidation and global deprotection to complete the syntheses.It is noteworthy that the 3-O-protecting group in the 2-deoxydisaccharide donors is found to be crucial for a successful N-glycosylation to assemble the cytosaminomycin disaccharide nucleosides.

关 键 词：Total synthesis GLYCOSYLATION NUCLEOSIDE Amicetin Cytosaminomycin 

分 类 号：O62[理学—有机化学]