SEQUENCING

Reaction Sequencing: A concise asymmetric approach to the antibacterial pleuromutilin

Coordinatore	THE UNIVERSITY OF MANCHESTER    more  Organization address address: OXFORD ROAD city: MANCHESTER postcode: M13 9PL contact info Titolo: Ms. Nome: Liz Cognome: Fay Email: send email Telefono: +44 161 275 7114 Fax: +44 161 275 2445
Nazionalità Coordinatore	United Kingdom [UK]
Totale costo	169˙390 €
EC contributo	169˙390 €
Programma	FP7-PEOPLE Specific programme "People" implementing the Seventh Framework Programme of the European Community for research, technological development and demonstration activities (2007 to 2013)
Code Call	FP7-PEOPLE-2007-2-1-IEF
Funding Scheme	MC-IEF
Anno di inizio	2008
Periodo (anno-mese-giorno)	2008-03-03   -   2008-11-02

 Partecipanti

#	participant	country	role	EC contrib. [€]
1	THE UNIVERSITY OF MANCHESTER  Organization address address: OXFORD ROAD city: MANCHESTER postcode: M13 9PL contact info Titolo: Ms. Nome: Liz Cognome: Fay Email: send email Telefono: +44 161 275 7114 Fax: +44 161 275 2445	UK (MANCHESTER)	coordinator	0.00

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 Obiettivo del progetto (Objective)

'Resistance to antibiotics is a major concern worldwide and has led to an urgent need to identify antibacterial agents with modes of action distinct from the established classes. The antibacterial natural product pleuromutilin is such a candidate and has been the focus of biological and medicinal studies in recent years. Unfortunately, pleuromutilin has poor pharmacokinetic properties and the compound is readily metabolised by enzymes. Although the natural product itself is not a very good drug, analogues of pleuromutilin look promising. This project will provide access to analogues of the natural product with drug–like properties that cannot currently be prepared, thus paving the way for new therapeutics based on the pleuromutilin scaffold that will improve the quality of life of people in the European Community We will develop new stereoselective processes in which the sequencing of a number of individual chemical reactions allows access to a complex, cyclic system in one synthetic step, using one reagent. We will assemble the skeleton of the antibacterial, pleuromutilin using the lanthanide reagent SmI2 to orchestrate the reaction sequencing so that we get a high yield while achieving good control over the stereochemistry of the product. Our proposal is that different parts of a molecule will react one after the other in an ordered sense, like toppling dominos, until a pleuromutilin–like product is reached. The results of our work will be of interest to synthetic chemists working in academic and industrial laboratories in Europe and throughout the world. The specific objectives of the multidisciplinary project are: - to investigate the individual reaction steps of the proposed sequence using model compounds. - to develop reaction sequencing in a concise synthesis of the tricyclic core of pleuromutilin. - to develop the first asymmetric route to pleuromutilin. - to prepare analogues of pleuromutilin and to carry out their preliminary biological evaluation.'