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Asymmetric Organocatalysed Diels-Alder/Fragmentation Cascades

Cel

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.

Zaproszenie do składania wniosków

FP7-PEOPLE-2009-IEF
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Koordynator

THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD
Wkład UE
€ 173 240,80
Adres
WELLINGTON SQUARE UNIVERSITY OFFICES
OX1 2JD Oxford
Zjednoczone Królestwo

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Region
South East (England) Berkshire, Buckinghamshire and Oxfordshire Oxfordshire
Rodzaj działalności
Higher or Secondary Education Establishments
Kontakt administracyjny
Linda Pialek (Ms.)
Linki
Koszt całkowity
Brak danych