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Issue 8, 2013
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Unexpected N-glycosidation reaction of glycals with 1-amino-anthracene: structure revision and application to the synthesis of new analogues of marmycin A

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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.

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

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Publication details

The article was received on 17 Oct 2012, accepted on 12 Dec 2012 and first published on 12 Dec 2012


Article type: Paper
DOI: 10.1039/C2OB27020J
Org. Biomol. Chem., 2013,11, 1383-1389

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

    X. Zhang, X. Jiang, C. Ding, Q. Yao and A. Zhang, Org. Biomol. Chem., 2013, 11, 1383
    DOI: 10.1039/C2OB27020J

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