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Title: Towards the total synthesis of phacelocarpus-2-pyrone A : novel 2-pyrone chemistry
Author: Burns, Michael John
ISNI:       0000 0004 2720 6578
Awarding Body: University of York
Current Institution: University of York
Date of Award: 2010
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This thesis describes the progress made towards the synthesis of the natural product phacelocarpus-2-pyrone A and the development of novel synthetic methodology for the synthesis of functionalised 2-pyrones. Initial studies focused on the synthesis of the natural product and the applications of Pd-catalysed cross-coupling reactions using the interesting palladium catalyst, CatCat. Key findings in the studies towards the natural product include: i) the synthesis of two 6-alkyl-4-hydroxy-2-pyrone intermediates suitable for providing a synthetic platform for future work; ii) the first synthesis of a 2-pyrone bound vinyl ether; iii) the synthesis of a 19 membered macrocycle containing 2-pyrone and 1,4-en-yne functionality. In addition, the first Pd-catalysed intramolecular C-H arylation of a 2-pyrone has been developed and applied to a number of substrates.
Supervisor: Fairlamb, Ian J. S. ; Taylor, Richard J. K. Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available