Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A
Zhang, Xuefeng2; Jiang, Xiaolong1; Ding, Chunyong2; Yao, Qizheng1; Zhang, Ao2
刊名ORGANIC & BIOMOLECULAR CHEMISTRY
2013
卷号11期号:8页码:1383-1389
ISSN号1477-0520
DOI10.1039/c2ob27020j
文献子类Article
英文摘要An unexpected N-glycosidation reaction of anthracen-1-amine with glycals was identified, and its use in the synthesis of C1' N-linked analogues of natural product marmycin A was explored. The structures of all these products were determined by 1D and 2D NMR, CD spectra, and X-ray crystal analysis. These products were then subjected to Friedel-Crafts acylation, Dess-Martin oxidation and nucleophilic addition leading to novel natural product analogues bearing a quaternary carbon center.
资助项目Distinguished Young Scholars of Chinese NSF[81125021] ; Chinese National Science Foundation[81072528] ; National Science & Technology Major Project on 'Key New Drug Creation and Manufacturing Program', China[2012ZX09103-101-035] ; National Science & Technology Major Project on 'Key New Drug Creation and Manufacturing Program', China[2012ZX09301001-001] ; Shanghai Commission of Science and Technology[10410702600] ; Shanghai Commission of Science and Technology[10JC1417100] ; Shanghai Commission of Science and Technology[10dz1910104] ; "Interdisciplinary Cooperation Team" Program for Science and Technology Innovation of the Chinese Academy of Sciences[00000000] ; State Key Laboratory of Medical Neurobiology and Collaborative Innovation Center for Brain Function and Remodeling[00000000]
WOS关键词CATALYZED CYCLIZATION ; TETRAHYDROQUINOLINES ; ANTIBIOTICS ; ACIDS
WOS研究方向Chemistry
语种英语
出版者ROYAL SOC CHEMISTRY
WOS记录号WOS:000314368200014
内容类型期刊论文
源URL[http://119.78.100.183/handle/2S10ELR8/277821]  
专题药物化学研究室
通讯作者Yao, Qizheng
作者单位1.China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Synthet Organ & Med Chem Lab, Shanghai 201203, Peoples R China;
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GB/T 7714
Zhang, Xuefeng,Jiang, Xiaolong,Ding, Chunyong,et al. Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2013,11(8):1383-1389.
APA Zhang, Xuefeng,Jiang, Xiaolong,Ding, Chunyong,Yao, Qizheng,&Zhang, Ao.(2013).Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A.ORGANIC & BIOMOLECULAR CHEMISTRY,11(8),1383-1389.
MLA Zhang, Xuefeng,et al."Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A".ORGANIC & BIOMOLECULAR CHEMISTRY 11.8(2013):1383-1389.
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