| EPSRC Reference: |
GR/M87344/01 |
| Title: |
SYNTHESIS OF SUGAR DERIVATIVES BY THE CYCLISATION OF ALLENE ESTERS |
| Principal Investigator: |
Knight, Dr J |
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| Project Partners: |
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| Department: |
School of Chemistry |
| Organisation: |
Newcastle University |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 October 2000 |
Ends: |
30 September 2003 |
Value (£): |
66,970
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| EPSRC Research Topic Classifications: |
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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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We have recently developed a new route to delta-lactones from readily available alkynyldioxolanone precursors. We propose to establish the scope of this chemistry by: variation of the level of substitution of the precursors; the use of alkynyloxiranes; and variation of the nucleophile. We will also investigate the stereochemical course of the reactions. In order to exemplify the work, we will use the chemistry developed to synthesise two unusual naturally occurring sugars. The extension of this work to the synthesis of (1-3) -C-linked disaccharides by the reaction of radical donors with allene esters is proposed. The regio- and stereo-chemical issues involved in this process will be investigated. We also propose to extend the chemistry to include the use of alkynyloxazolidinones. These compounds may be synthesised in enantiomerically pure form from readily available amino acid precursors. This should provide a new route to iminosugars and indolizidine alkaloids and complements our existing palladium catalysed carbonylation of vinyloxazolidinones. The proposed chemistry will be applicable to the synthesis of a range of biologically important compounds such as monosaccharides, glycopeptide precursors, C-disaccharides, iminosugars, and alkaloids.
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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 |