| EPSRC Reference: |
GR/R19885/01 |
| Title: |
The Osmium Promoted Oxidative Cyclisation of Polyenes |
| Principal Investigator: |
Donohoe, Professor T |
| Other Investigators: |
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| Researcher Co-Investigators: |
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| Project Partners: |
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| Department: |
Oxford Chemistry |
| Organisation: |
University of Oxford |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 October 2001 |
Ends: |
30 September 2004 |
Value (£): |
85,875
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| EPSRC Research Topic Classifications: |
| Biological & Medicinal Chem. |
Chemical Synthetic Methodology |
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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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The proposal maps out a study or me osmium promoted cylisation of dienes to yield tetrahydrofurams. We have discovered that osmium tetroxide is capable of turning 1,5-dienes into tetrahydrofurans with high yields and stereoselectivity. This method is inherently valuable because tetrahydrofurans are important constituents of many biologically active natural products and so there is an immediate potential for the products that we shall make.We shall begin by investigating the scope of the cyclisation reaction and look at a variety of different 1,5- (and 1,6-) dienes; the case for both stereospecificity and stereoselectivity will be examined. This information will tell us more about the mechanism of the reaction and we aim to investigate a variety of different conditions and catalysts for the cyclisation. We are able to separate the two distinct steps in the reaction, initiation and cyclisation, and this will prove very useful in understanding and optimising the chemistry and should lead to a general purpose method for tetrahydrofuran formation. Our next goal will be control of absolute stereochemistry, which is essential in the medium term. We will investigate two main approaches (i) to make chiral initiator groups and examine diastereoselective cyclisation reactions; (ii) the use of chiral ligands for osmium tetroxide so as to enforce absolute stereochemistry on prochiral diene substrates.We think that the range of reactions likely to be encountered in this project, ie preparation of the cyclisation precursors, the cyclisation reaction itself and suitable derivatisation afterwards, will provide an excellent training for a PhD student.
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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.ox.ac.uk |