Aminocyclopropanes as precursors of endoperoxides with antimalarial activity
Identifieur interne : 000599 ( Istex/Checkpoint ); précédent : 000598; suivant : 000600Aminocyclopropanes as precursors of endoperoxides with antimalarial activity
Auteurs : Claire Madelaine [France] ; Olivier Buriez [France] ; Benot Crousse [France] ; Isabelle Florent [France] ; Philippe Grellier [France] ; Pascal Retailleau [France] ; Yvan Six [France]Source :
- Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2010.
English descriptors
- Teeft :
- Abxy system, Abxyz system, Alumina, Amide, Aminocyclopropanation reactions, Aminocyclopropane, Aminocyclopropanes, Angew, Anodic compartment, Bicyclic, Bicyclic aminocyclopropanes, Biomol, Cdcl3, Characteristic signals, Chcf3, Chem, Colourless, Crude product, Crude products, Cyclic, Cyclic voltammetry, Diastereoisomeric, Diastereoisomeric aminocyclopropane products, Diastereoisomeric endoperoxide products, Diastereoisomers, Diethyl ether, Double bond, Endoperoxide, Endoperoxides, Equiv, Falciparum, Flash chromatography, General procedure, Hco2, Hco2 hco2, Hplc, Intramolecular, Intramolecular meijere reactions, Meijere, Mmol, Neutral alumina, Nitrogen atom, Plasmodium, Plasmodium falciparum, Potential values, Preparative hplc, Retention time, Royal society, Small amount, Substituent, Voltammetry.
Abstract
This contribution describes the synthesis of several novel bicyclic -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 (Kulinkovichde 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:
DOI: 10.1039/c0ob00308e
Affiliations:
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<term>Aminocyclopropane</term>
<term>Aminocyclopropanes</term>
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<front><div type="abstract">This contribution describes the synthesis of several novel bicyclic -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 (Kulinkovichde 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.</div>
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