| EPSRC Reference: |
GR/M08967/02 |
| Title: |
THE SYNTHESIS OF GEM-DIFLUOROSHIKIMIC ACID DERIVATIVES |
| Principal Investigator: |
Whitehead, Dr R |
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| Department: |
Chemistry |
| Organisation: |
Victoria University of Manchester, The |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 July 1999 |
Ends: |
31 December 2001 |
Value (£): |
36,721
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| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
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| No relevance to Underpinning Sectors |
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Summary on Grant Application Form |
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In the first instance, the aim of the research outlined in this proposal is to optimise our recently developed methodology for the preparation of allylic gem-difluoromethylene compounds. The procedure involves the application of ultra-high pressure to the DAST mediated nucleophilic fluorination of the corresponding unsaturated carbonyl compounds. Having achieved this goal, we wish to exploit the procedure in the preparation of gram-quantities of 1-iodo- and 1-bromo-6, 6-difluorocyclohexene and to subsequently examine the behaviour of these compounds in palladium catalysed coupling reactions and in trans-matallation chemistry in order to prepare 6, 6-difluoro-cyclohexene-1-carboxylic acid.The development of an efficient synthesis of this compound will then allow us to turn our attention to the synthesis of 6, 6-difluoroshikimic acid, a potential anti-bacterial agent, utilising the cyclohexa-3, 5-diene-1, 2-diol derived from microbial oxidation of bromobenzene. The successful outcome of this synthesis will represent an excellent example of the application of the high pressure methodology to an extremely challenging target. If time allows, we will also apply the technology to the preparation of 3-deoxy-3, 3-difluoroshikimic acid, a possible inhibitor of shikimate dehydrogenase.
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Key Findings |
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Potential use in non-academic contexts |
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Impacts |
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| Description |
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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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