| EPSRC Reference: |
GR/N31054/01 |
| Title: |
AN AZA-(2,3)-WITTIG REARRANGEMENT STATEGY FOR THE ENAN TIOSELECTIVE SYNTHESIS OF THE PINNAIC ACIDS |
| Principal Investigator: |
Stockman, Professor RA |
| Other Investigators: |
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| Project Partners: |
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| Department: |
Chemistry |
| Organisation: |
University of East Anglia |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
02 October 2000 |
Ends: |
01 October 2003 |
Value (£): |
63,162
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| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
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| EPSRC Industrial Sector Classifications: |
| Pharmaceuticals and Biotechnology |
No relevance to Underpinning Sectors |
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Summary on Grant Application Form |
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The aza-Wittig rearrangement of vinyl aziridines is a known, but underdeveloped area of heterocyclic chemistry. The proposed programme of research will investigate further this reaction, extending the scope of the reaction to include bicyclic systems. This will allow the formation of a variety of fused, bridged and spirocyclic tetrohydropyridine derivatives. An investigation into the direct synthesis of vinyl aziridines by the reaction of allyl carbene equivalents with unactivated imines will also be carried out. Having completed studies on the scope and limitations of the aza-Wittig rearrangement of bicyclic vinyl aziridines, this strategy will be applied to the synthesis of two related biologically interesting natural products, pinnaic acid and tauropinnaic acid. Both compounds were found to exhibit inhibitory activity towards phospholipase A2 in vitro, thus these compounds are potentially useful as anti-inflammatory agents. Total synthesis will also prove unambiguously their relative and absolute stereochemistry.
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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.uea.ac.uk |