Aminocyclopropanes as precursors of endoperoxides with antimalarial activity

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TitleAminocyclopropanes as precursors of endoperoxides with antimalarial activity
Publication TypeJournal Article
Year of Publication2010
AuthorsMadelaine, C, Buriez O, Crousse B, Florent I, Grellier P, Retailleau P, Six Y
JournalOrganic & Biomolecular Chemistry
Volume8
Issue24
Pagination5591-5601
ISBN Number1477-0520
Accession NumberISI:000284610600016
Abstract

This contribution describes the synthesis of several novel bicyclic alpha-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.

URL<Go to ISI>://000284610600016
DOI10.1039/c0ob00308e
Short TitleAminocyclopropanes as precursors of endoperoxides with antimalarial activity
Unit: 
UMR 8640