Asymmetric Organocatalysed Diels-Alder/Fragmentation Cascades

Projektinformationen

ASODAFCA

ID Finanzhilfevereinbarung: 254068

Projekt abgeschlossen

Startdatum 1 März 2010

Enddatum 29 Februar 2012

Finanziert unter

• Specific programme "People" implementing the Seventh Framework Programme of the European Community for research, technological development and demonstration activities (2007 to 2013)

Gesamtkosten € 173 240,80

EU-Beitrag € 173 240,80

Koordiniert durch

THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD
United Kingdom

Ziel

The intramolecular Diels-Alder reaction of 2-amino-furan derivatives is a powerful tool for the rapid synthesis of complex polycyclic compounds. The reaction has been used as a key step in the preparation of biologically relevant molecules such as natural products and pharmaceuticals. However, despite the great potential of this kind of Diels-Alder reaction, no catalytic asymmetric version has been reported so far. During this Fellowship we wish to develop new, asymmetric, organocatalysed cyclisation reactions of substrates bearing an amino-furan derivative and an enone functionality. In the presence of primary or secondary chiral amines, alpha,beta-unsaturated compounds undergo LUMO-lowering activation via the reversible formation of transient iminium ions. The concept of our proposal is to apply the iminium ion activation of enones to induce asymmetry in the Diels-Alder cycloaddition with appended amino-furan moieties. Furthermore, it is known that stereocenters at the gamma-position of enones can be racemised in the presence of primary/secondary amines via the formation of dienamine intermediates. Therefore, a further target will be the development of a tandem transformation involving a Dynamic Kinetic Resolution (DKR) and an Intramolecular Diels-Alder reaction of 2-amino-furan derivatives with enones presenting a stereogenic centre at the gamma-carbon. This would constitute a new, powerful and broadly applicable organocatalytic asymmetric strategy to target, in the first instance, alkaloids of the Daphniphyllum family. In particular, we are interested in the enantioselective synthesis Daphniyunnine D (IC50 0.6 μM against A549 cancer cell line). The Fellowship will therefore involve different branches of modern chemical research, such as asymmetric methodology, catalysis, target oriented synthesis of bioactive compounds.

Wissenschaftliches Gebiet

• medical and health sciences › basic medicine › pharmacology and pharmacy › pharmaceutical drugs
• medical and health sciences › clinical medicine › oncology
• natural sciences › chemical sciences › catalysis
• natural sciences › chemical sciences › organic chemistry › amines

Programm/Programme

• FP7-PEOPLE - Specific programme "People" implementing the Seventh Framework Programme of the European Community for research, technological development and demonstration activities (2007 to 2013)

Thema/Themen

• FP7-PEOPLE-2009-IEF - Marie Curie Action: "Intra-European Fellowships for Career Development"

Aufforderung zur Vorschlagseinreichung

FP7-PEOPLE-2009-IEF
Andere Projekte für diesen Aufruf anzeigen

Finanzierungsplan

MC-IEF - Intra-European Fellowships (IEF)

Koordinator

THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD

Kontakt Verwaltung

Linda Pialek (Ms.)

• EU-Beitrag: € 173 240,80
• Adresse: WELLINGTON SQUARE UNIVERSITY OFFICES ; OX1 2JD Oxford ; Vereinigtes Königreich
• Region: South East (England) › Berkshire, Buckinghamshire and Oxfordshire › Oxfordshire
• Aktivitätstyp: Higher or Secondary Education Establishments
• Gesamtkosten: Keine Daten