Issue 21, 2011
From the journal:

Organic & Biomolecular Chemistry

Stereoselective synthesis and rearrangement-fragmentation of arylidene N-alkoxydiketopiperazines†

Shouxin Liu,*ab   Yun Mu,a   Jianrong Han,a   Xiaoli Zhen,a   Yihua Yang,a   Xia Tiana  and  Andrew Whiting*b  

* Corresponding authors

a State Key Laboratory Breeding Base-Hebei Province Key Laboratory of Molecular Chemistry for Drug, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
E-mail: shouxin.liu@durham.ac.uk

b Centre for Sustainable Chemical Processes, Department of Chemistry, Durham University, Science Laboratories, South Road, Durham, United Kingdom
E-mail: andy.whiting@durham.ac.uk
Fax: (+44)-191-386 1127

Abstract

A stereoselective synthesis of arylidene N-alkoxydiketopiperazines viaoxime-ether formation and intramolecular acylation is described, followed by an acid-catalysed rearrangement-fragmentation to give novel diketopiperazine hemiaminal derivatives with useful bioactivity against certain tumour cell lines.

Graphical abstract: Stereoselective synthesis and rearrangement-fragmentation of arylidene N-alkoxydiketopiperazines

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Article information

DOI
https://doi.org/10.1039/C1OB05722G
Article type
Paper
Submitted
06 May 2011
Accepted
05 Aug 2011
First published
08 Aug 2011

Org. Biomol. Chem., 2011,9, 7476-7481

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Stereoselective synthesis and rearrangement-fragmentation of arylidene N-alkoxydiketopiperazines

S. Liu, Y. Mu, J. Han, X. Zhen, Y. Yang, X. Tian and A. Whiting, Org. Biomol. Chem., 2011, 9, 7476 DOI: 10.1039/C1OB05722G

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