| EPSRC Reference: |
GR/M55565/01 |
| Title: |
USE OF PHOSPHITE OZONE ADDUCTS FOR THE SYNTHESIS OF 1,2,4-TRIOXANE AND ENDOPEROXIDE ANTIMALARIAL DRUGS |
| Principal Investigator: |
ONeill, Prof. P |
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| Department: |
Chemistry |
| Organisation: |
University of Liverpool |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 June 1999 |
Ends: |
30 September 2000 |
Value (£): |
52,409
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| EPSRC Research Topic Classifications: |
| Biological & Medicinal Chem. |
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| No relevance to Underpinning Sectors |
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Summary on Grant Application Form |
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This proposal concerns the development of novel phosphite-based singlet oxygen sources for use in organic synthesis. The phosphite ozone adducts are easy to prepare from cheap, readily available starting materials and their use has several advantages over traditional photooxidative methods for generation of singlet oxygen. We will evaluate the use of the known triphenyl phosphite adduct (TRIPOA) and our new phosphite ozone complexes in three typical reactions of singlet oxygen, including: i) the formation of dioxetanes and further elaboration into 1, 2, 4-trioxane systems, ii) (4+2) cycloadditions of singlet oxygen to diene systems and iii) the ene reaction of suitably functionalised alkenes. Comparison of the reactivity of these reagents in terms of yield, stereo-selectivity and scale will be made with photooxidation conditions using methylene blue as sensitiser. Following optimisation with these reagents, the new methodology will be applied to the total synthesis of the natural product (+) -artemisinin and to the synthesis of a new class of peroxide cysteine protease inhibitor pro-drugs.
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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.liv.ac.uk |