Towards the total synthesis of Phacelocarpus-2-pyrone A: Novel 2-pyrone chemistry

Abstract

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.