title: Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A.
abstract: 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.
authors: CAS Key Laboratory of Receptor Research, Synthetic Organic & Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.
authors: Xuefeng
authors: X
authors: Zhang
authors: Xiaolong
authors: X
authors: Jiang
authors: Chunyong
authors: C
authors: Ding
authors: Qizheng
authors: Q
authors: Yao
authors: Ao
authors: A
authors: Zhang
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: D000880:Anthraquinones; D006027:Glycosides; C524224:marmycin A