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dc.contributor.advisorWestwood, Nicholas James
dc.contributor.authorLancefield, Christopher Stuart
dc.description.abstractThe first part of this thesis describes my research towards the valorisation of lignin. Due to environmental and political pressures, there has been a drive to start the transition from a fossil fuel based economy to a renewable based one. This will require the development of novel routes to renewable chemicals, one source of which may be the biopolymer lignin. Through the synthesis of advanced lignin model compounds, the chemistry of real lignin is explored. This work culminates in the development of a novel method for the depolymerisation of real lignin to simple mixtures of aromatic chemicals that could be useful building blocks for the chemical industry. One of the key steps in this process is the oxidation of the β-O-4 linkages in lignin using catalytic amounts of DDQ and molecular oxygen as the terminal oxidant. The second part of this thesis details the first synthesis of melohenine B and O-ethyl-14-epimelohenine B, two medium sized ring containing natural products. The key step in the synthesis of these natural products was the photo-sensitised oxidative cleavage of an indolic substrate by molecular oxygen. Additionally, the use of residual dipolar coupling (RDC) analysis for the conformational analysis of these molecules in solution has been explored. Finally, the absolute configurational assignment of the natural products was established and their biological activities investigated.en_US
dc.publisherUniversity of St Andrews
dc.rightsCreative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
dc.subjectMelohenine Ben_US
dc.subjectNatural producten_US
dc.subject.lcshNatural products--Synthesisen_US
dc.titleUsing molecular oxygen in synthesis : applications in lignin valorisation and natural product synthesisen_US
dc.type.qualificationnamePhD Doctor of Philosophyen_US
dc.publisher.institutionThe University of St Andrewsen_US
dc.rights.embargoreasonThesis restricted in accordance with University regulations. Print and electronic copy restricted until 10th October 2018en_US

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Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
Except where otherwise noted within the work, this item's licence for re-use is described as Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International