White Rose University Consortium logo
University of Leeds logo University of Sheffield logo York University logo

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

Burns, Michael John (2010) Towards the total synthesis of Phacelocarpus-2-pyrone A: Novel 2-pyrone chemistry. PhD thesis, University of York.

[img] Text (MBurns PhD thesis)
MBurns_PhD_Thesis.pdf
Available under License Creative Commons Attribution-Noncommercial-No Derivative Works 2.0 UK: England & Wales.

Download (3155Kb)

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.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Depositing User: Mr Michael John Burns
Date Deposited: 19 Oct 2010 15:32
Last Modified: 08 Aug 2013 08:45
URI: http://etheses.whiterose.ac.uk/id/eprint/1059

Actions (repository staff only: login required)