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Synthetic approaches to polyoxygenated chromone and chromanome natural products

Wootton, RCR 2000, Synthetic approaches to polyoxygenated chromone and chromanome natural products , PhD thesis, University of Salford, UK.

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    Abstract

    The work described in this thesis is concerned with the chemistry of polymethoxylated aromatic carbonyl compounds bearing a 2,6-dioxygenated substitution pattern, with particular regard to establishing synthetic routes to biologically active chromone and chromanone systems. Syntheses of key intermediates in the approaches to the natural products stigmatellin, baicalein and LL-D253(x (and related products) were undertaken. In chapter one the reactions of nucleophiles at the carbonyl moieties of 2,6- dioxygenated benzene carbonyl compounds are reviewed. This type of process o can present special difficulties and was to prove particularly significant at various stageso f the work describedi n subsequenct hapters. Chapter two is a review of the provenance, abundance, biosynthesis, and previous syntheses of the natural products stigmatellin, baicalein and LL-D253(x, these being the targets of the synthetic work undertaken in the course of the project. Chapter three is concerned with an approach to a fragment of the stigmatellin molecule (referred to as stigmatellin fragment A) using the Vilsmeier formylation reaction, while chapter four is concerned with an alternative approach to stigmatellin fragment A using Friedel-Crafts acylation methodology. The strategies and the results obtained are described and analysed in detail. In chapter five a strategy for the synthesis of baicalein trimethyl ether is described and the results obtained are discussed.

    Item Type: Thesis (PhD)
    Contributors: Wallace, TD(Supervisor)
    Additional Information: PhD supervisor: Dr. Tim Wallace
    Themes: Subjects / Themes > Q Science > QD Chemistry
    Subjects outside of the University Themes
    Schools: Colleges and Schools > College of Science & Technology
    Colleges and Schools > College of Science & Technology > School of Computing, Science and Engineering
    Depositing User: Institutional Repository
    Date Deposited: 01 Jul 2009 16:34
    Last Modified: 19 Feb 2014 15:26
    URI: http://usir.salford.ac.uk/id/eprint/2171

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