Issue 8, 2013
From the journal:

Organic & Biomolecular Chemistry

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,‡a   Xiaolong Jiang,‡b   Chunyong Ding,a   Qizheng Yao*b  and  Ao Zhang*a  

* Corresponding authors

a CAS Key Laboratory of Receptor Research, Synthetic Organic & Medicinal Chemistry Laboratory (SOMCL), Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences, Shanghai, China
E-mail: aozhang@mail.shcnc.ac.cn
Fax: +86-21-50806035
Tel: +86-21-50806035

b Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
E-mail: qz_yao@yahoo.com.cn

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB27020J
Article type
Paper
Submitted
17 Oct 2012
Accepted
12 Dec 2012
First published
12 Dec 2012

Org. Biomol. Chem., 2013,11, 1383-1389

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements