Issue 24, 2010
From the journal:

Organic & Biomolecular Chemistry

Aminocyclopropanes as precursors of endoperoxides with antimalarial activity†

Claire Madelaine,a   Olivier Buriez,*b   Benoît Crousse,c   Isabelle Florent,d   Philippe Grellier,d   Pascal Retailleaua  and  Yvan Six*ae  

* Corresponding authors

a Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France

b École Normale Supérieure, Département de Chimie, UMR 8640 CNRS-ENS-UPMC, F75231 Paris, France

c Laboratoire BioCIS-CNRS, Faculté de Pharmacie, Université Paris-Sud 11, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France

d Muséum National d′Histoire Naturelle, FRE 3206 CNRS, 61 rue Buffon, 75231 Paris Cedex 05, France

e Present address: Département de Chimie, UMR 7652, CNRS/Ecole Polytechnique, 91128 Palaiseau, France
E-mail: six@dcso.polytechnique.fr
Fax: +33(0)1 6933 5972
Tel: +33(0)1 6933 5979

Abstract

This contribution describes the synthesis of several novel bicyclic α-amino endoperoxides, including CF3-substituted compounds, prepared by the aerobic electrochemical oxidation of a family of bicyclic aminocyclopropanes. These, in turn, are readily synthesised by a titanium-mediated intramolecular cyclopropanation process (Kulinkovich–de Meijere reaction), starting from N-alkenyl amides that contain a vic-disubstituted double bond, with high diastereoselectivity. An evaluation of the biological activities of several of the molecules produced, against the parasite Plasmodium falciparum, is also presented.

Graphical abstract: Aminocyclopropanes as precursors of endoperoxides with antimalarial activity

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C0OB00308E
Article type
Paper
Submitted
23 Jun 2010
Accepted
03 Sep 2010
First published
03 Sep 2010

Org. Biomol. Chem., 2010,8, 5591-5601

Permissions

Request permissions

Aminocyclopropanes as precursors of endoperoxides with antimalarial activity

C. Madelaine, O. Buriez, B. Crousse, I. Florent, P. Grellier, P. Retailleau and Y. Six, Org. Biomol. Chem., 2010, 8, 5591 DOI: 10.1039/C0OB00308E

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