Stephens, Tom (2019) Successive Ring Expansion Reactions. PhD thesis, University of York.
Abstract
This thesis describes the development of a series of methods for performing ring expansion reactions consecutively, either using successive reactions (explored in Chapters 2–4) or cascade sequences (explored in Chapters 5 and 6).
In Chapter two, β-ketoester ring expansion methodology (that has been developed in the Unsworth group) has been extended by incorporating both amino acids and β-hydroxy acids into a range of previously inaccessible cyclic starting materials. The molecular properties of the compounds were then examined to assess their ‘lead-likeliness’. In Chapter three, the simple lactam motif was utilised to incorporate α-/β-amino acids to produce macrocyclic peptidiomimetics directly, with a range of natural α-amino acids incorporated. In Chapter four, lactams were then ring enlarged with hydroxy acids forming a diverse array of functionalised macrocyclic lactones. In Chapter five, a cyclisation/expansion cascade was collaboratively explored forming medium-sized bi-aryl lactones/lactams with excellent atroposelectivity. Chapter six describes the preliminary results obtained, for a similar cyclisation/expansion cascade (towards the synthesis of polyamine macrocycles), whereby consecutive acyl transfer reactions must occur.
Metadata
Supervisors: | Unsworth, William and Fascione, Martin and O'Brien, Peter |
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Awarding institution: | University of York |
Academic Units: | The University of York > Chemistry (York) |
Identification Number/EthosID: | uk.bl.ethos.829744 |
Depositing User: | Mr Tom Stephens |
Date Deposited: | 10 May 2021 19:26 |
Last Modified: | 21 Jun 2021 09:53 |
Open Archives Initiative ID (OAI ID): | oai:etheses.whiterose.ac.uk:24931 |
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