Issue 21, 2008
From the journal:

Organic & Biomolecular Chemistry

Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds†

Daniel Farran,a   Isabelle Parrot,a   Loïc Toupet,b   Jean Martineza  and  Georges Dewynter*a  

* Corresponding authors

a Institut des Biomolécules Max Mousseron, UMR CNRS 5247, Université Montpellier 1, Université Montpellier 2, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France
E-mail: dewynter@univ-montp2.fr

b Groupe Matière Condensée et Matériaux, UMR 6626, Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France

Abstract

An efficient and original stereocontrolled transannular rearrangement starting from activated 2,5-diketopiperazines has been developed, an opportunity for the medicinal chemistry field, which requests access to novel biological scaffolds. This powerful ring contraction, which can be related to a stereoselective aza-version of the Chan rearrangement, allows for example the one-step synthesis of various tetramic acids, access to 2-disubstituted statins, or the synthesis of relevant lactam-constrained dipeptide mimetics using a TRAL–RCM sequence.

Graphical abstract: Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds

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Article information

DOI
https://doi.org/10.1039/B810352F
Article type
Paper
Submitted
18 Jun 2008
Accepted
24 Jul 2008
First published
03 Sep 2008

Org. Biomol. Chem., 2008,6, 3989-3996

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Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds

D. Farran, I. Parrot, L. Toupet, J. Martinez and G. Dewynter, Org. Biomol. Chem., 2008, 6, 3989 DOI: 10.1039/B810352F

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