ENACASCASYN
Enantioselective Organocatalytic Reaction Cascades of Substituted Pyrroles and their Application in Complex Alkaloid Natural Product Synthesis
| 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 | 200˙049 € |
| EC contributo | 200˙049 € |
| 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-2010-IEF |
| Funding Scheme | MC-IEF |
| Anno di inizio | 2011 |
| Periodo (anno-mese-giorno) | 2011-09-01 - 2013-08-31 |
Partecipanti
| # | ||||
|---|---|---|---|---|
| 1 |
THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD
Organization address
address: University Offices, Wellington Square contact info |
UK (OXFORD) | coordinator | 200˙049.60 |
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Obiettivo del progetto (Objective)
'Tracking the footsteps of nature, organocatalytic systems allow the formation of highly enantioenriched products starting from simple achiral substrates. Within this context, enantioselective organocatalytic cascade reactions have emerged as a powerful tool for the design of complex molecular architectures in single-step conversions. During this Fellowship we intend, in a very early stage, to address new, straightforward and synthetically powerful enantioselective cascade reactions towards the complex perhydroindole ring structure; a saturated and functionalized 6,5-fused bicycle system which is present in several targets with significant biological activities. Specifically, our methodology will be supported by the development of new asymmetric, organo-catalysed Michael, Michael cyclization cascades of activated pyrrole substrates with α,β-unsaturated ketones. In this sense our proposal takes advantage of the chemical reactivity of activated pyrrole substrates, based on their high acidity, and therefore tendency to enolisation giving the tautomeric nucleophilic form. This species can react with electron deficient alkenes by means of an organo-catalysed Michael addition. At this point, favoring the optimal catalytic conditions, we have envisioned that the intermediate Michael adduct can undergo an intramolecular Michael addition cascade to afford the desired bicycle target. Highlighting the scope of our approach towards the perhydroindole ring core, we are aiming to accomplish the first total synthesis of Daphhniyunnine D, a complex and important alkaloid recently isolated from a shrub endemic of the Peoples Republic of China, and with a prominent cytotoxic activity against several tumor cell lines. The Fellowship will touch therefore contemporary areas of modern chemical research, such as asymmetric methodology, catalysis and target oriented synthesis approaches towards bioactive compounds.'