| EPSRC Reference: |
GR/R74796/01 |
| Title: |
The Diazo Route to Diazonamide A |
| Principal Investigator: |
Moody, Professor CJ |
| Other Investigators: |
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| Researcher Co-Investigators: |
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| Project Partners: |
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| Department: |
Chemistry |
| Organisation: |
University of Exeter |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
05 March 2002 |
Ends: |
04 March 2005 |
Value (£): |
180,033
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| EPSRC Research Topic Classifications: |
| Biological & Medicinal Chem. |
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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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Diazonamide A is a structurally unique natural product isolated from a marine organism. It is characterised by the presence of four heterocyclic rings - a 2,3,4-trisubstituted indole, two 2,4,5-trisubstituted oxazoles and a dihydrobenzofuran - in a double macrocyclic array, and possesses excellent anticancer activity. The aim of the project is to complete the synthesis of this fascinating natural product.The proposed route identifies two key fragments: a tyrosine derived benzofuranone and a trisubstituted indole. New routes to the benzofuranone will be developed using carbene insertions and the Claisen rearrangement as key steps. After coupling to the indole fragment, two strategies for completion of the macrocydic core of the natural product will be investigated. Both involve the dirhodium(II) catalysed reactions of diazocarbonyl compounds, either in 'cycloaddition' to nitriles or in N-H insertion reactions of amides. Finally it is proposed to complete the synthesis by installation of the second chlorine atom and the valine side-chain.
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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.ex.ac.uk |