ASODAFCA
Asymmetric Organocatalysed Diels-Alder/Fragmentation Cascades
| Coordinatore | THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD
Organization address
address: University Offices, Wellington Square contact info |
| Nazionalità Coordinatore | United Kingdom [UK] |
| Totale costo | 173˙240 € |
| EC contributo | 173˙240 € |
| 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-2009-IEF |
| Funding Scheme | MC-IEF |
| Anno di inizio | 2010 |
| Periodo (anno-mese-giorno) | 2010-03-01 - 2012-02-29 |
Partecipanti
| # | ||||
|---|---|---|---|---|
| 1 |
THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD
Organization address
address: University Offices, Wellington Square contact info |
UK (OXFORD) | coordinator | 173˙240.80 |
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Obiettivo del progetto (Objective)
'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.'