| EPSRC Reference: |
GR/R00111/01 |
| Title: |
Palladium Mediated Synthesis of Biologically Important Hererocycles |
| Principal Investigator: |
Knight, Dr J |
| Other Investigators: |
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| Researcher Co-Investigators: |
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| Project Partners: |
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| Department: |
School of Chemistry |
| Organisation: |
Newcastle University |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
07 February 2001 |
Ends: |
06 February 2003 |
Value (£): |
117,894
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| EPSRC Research Topic Classifications: |
| Carbohydrate Chemistry |
Catalysis & Applied Catalysis |
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| EPSRC Industrial Sector Classifications: |
| Chemicals |
Pharmaceuticals and Biotechnology |
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| Related Grants: |
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| Panel History: |
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Summary on Grant Application Form |
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We have recently reported a new palladium catalysed carbonylation leading from S-vinyloxazolidinones (readily available in enantiomerically pure form from amino acids) to dihydropyridones. The products are ideally functionalised for elaboration into a range of biologically important heterocyclic targets. We aim to increase the synthetic potential of this novel reaction by: optimising the reaction conditions in terms of ligand, catalyst, pressure, and temperature; exploring the substrate scope and limitations; and elucidating the stereochemical course of the reaction. We then propose to illustrate the chemistry by applying it to the synthesis of several piperidine and ergot alkaloids.The extension of the cyclisation to the synthesis of five-membered heterocycles is then proposed by three routes: carbonylation of 4-methylene-2-oxazinones; cyclisation by intramolecular trapping of vinyloxazolidinone-derived pi-allyl intermediates carrying pendant nucleophiles; the use of pi-allyl intermediates as 1,3-dipoles for cycloaddition to suitable dienophiles.The chemistry developed should be applicable to the synthesis of a wide range of stereochemically and functionally complex heterocyclic targets.
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Key Findings |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Potential use in non-academic contexts |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Impacts |
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| Description |
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk |
| Summary |
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| Date Materialised |
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Sectors submitted by the Researcher |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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| Project URL: |
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| Further Information: |
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| Organisation Website: |
http://www.ncl.ac.uk |