Issue 65, 2012
From the journal:

Chemical Communications

Synthesis of strained cyclic peptides via an aza-Michael–acyl-transfer reaction cascade†

Jochem P. A. Rutters,a   Yvette Verdonk,a   Remko de Vries,a   Steen Ingemann,a   Henk Hiemstra,a   Vincent Levacherb  and  Jan H. van Maarseveen*a  

* Corresponding authors

a Van't Hoff Institute for Molecular Sciences, Science Park 904, 1098XH Amsterdam, The Netherlands
E-mail: j.h.vanmaarseveen@uva.nl
Fax: +31 205255604
Tel: +31 205255671

b Laboratoire de Chimie Organique Fine et Hétérocyclique UMR 6014 IRCOF, CNRS, Université et INSA de Rouen, B.P 08, F-76131 Mont-Saint-Aignan Cédex, France

Abstract

A new method is presented to prepare strained lactams. Esterification of the C-terminus of a dipeptide with β-nitrostyrene or quinoline-type auxiliaries is followed by lactam formation by an intramolecular aza-Michael–acyl-transfer reaction cascade. Ultimately, the cyclic tetrapeptide cyclo[Phe-Tyr-Ala-Gly] has been prepared.

Graphical abstract: Synthesis of strained cyclic peptides via an aza-Michael–acyl-transfer reaction cascade

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Article information

DOI
https://doi.org/10.1039/C2CC34121B
Article type
Communication
Submitted
08 Jun 2012
Accepted
25 Jun 2012
First published
26 Jun 2012

Chem. Commun., 2012,48, 8084-8086

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Synthesis of strained cyclic peptides via an aza-Michael–acyl-transfer reaction cascade

J. P. A. Rutters, Y. Verdonk, R. de Vries, S. Ingemann, H. Hiemstra, V. Levacher and J. H. van Maarseveen, Chem. Commun., 2012, 48, 8084 DOI: 10.1039/C2CC34121B

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