Diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis
This thesis describes the development of a new method to desymmetrise <i>meso</i>-succinic and glutaric anhydrides and its application in the synthesis of a fragment of the biologically active natural product rapamycin. It is divided into four chapters: - Chapter one provides an introduc...
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University of Cambridge
2007
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| Online Access: | http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.598878 |
| Summary: | This thesis describes the development of a new method to desymmetrise <i>meso</i>-succinic and glutaric anhydrides and its application in the synthesis of a fragment of the biologically active natural product rapamycin. It is divided into four chapters: - Chapter one provides an introduction to the concept of desymmetrisation, followed by a literature summary reviewing the history of anhydride desymmetrisation methodology over the past fifty years and application in natural product synthesis. - Chapter two describes the project background more specifically and the original project aims are delineated. - Chapter three presents the results and discussion: proof of concept is followed by application of the method to generate both acid-amide and ester-amide derivatives. Optimisation studies, scope of reaction and theoretical modelling studies are all incorporated within this section. A general background on the natural product rapamycin is then given, and use of the novel desymmetrisation methodology in the synthesis of a fragment of the interesting and challenging natural product is discussed. - Chapter four concludes the thesis and makes some suggestions for future work. - Chapter five provides a formal account of the experimental procedures. References and appendices containing supporting X-ray crystal structure data follow. |
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