Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A

Xuefeng Zhang; Xiaolong Jiang; Chunyong Ding; Qizheng Yao; Ao Zhang

doi:10.1039/c2ob27020j

Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A

Org Biomol Chem. 2013 Feb 28;11(8):1383-9. doi: 10.1039/c2ob27020j.

Authors

Xuefeng Zhang¹, Xiaolong Jiang, Chunyong Ding, Qizheng Yao, Ao Zhang

Affiliation

¹ CAS Key Laboratory of Receptor Research, Synthetic Organic & Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China.

PMID: 23328958
DOI: 10.1039/c2ob27020j

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthraquinones / chemical synthesis*
Anthraquinones / chemistry
Glycosides / chemistry*
Glycosylation
Models, Molecular
Molecular Conformation
Molecular Structure

Substances

Anthraquinones
Glycosides
marmycin A