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Title: Synthesis of eleutherobin-like potential microtubule stabilising agents
Author: Syntrivanis, Leonidas-Dimitrios
ISNI:       0000 0004 6500 7676
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 2017
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This thesis describes synthetic studies towards the tricyclic terpene framework of the cytotoxic natural product eleutherobin, and the investigation of biocatalytic methodology towards late stage functionalisation of the structure. Chapter 1 provides an introduction to the biomedical significance of the natural product and to the various synthetic studies reported to date. Chapter 2 explores intramolecular Diels-Alder approaches to the construction of the nine- and six- membered rings present in the natural product. Chapter 3 describes alternative approaches to the eleutherobin core structure, leading to a formal synthesis of the natural product. The synthetic sequence developed is applied to the preparation of a small library of furanoid analogues of eleutherobin. Chapter 4 details the development of methodology for the one-pot preparation of (E)-4-methylhexa-3,5-dien-1-ol, and its use in an intermolecular Diels-Alder/lactonisation sequence to achieve enantioselective preparation of an important lactone building block. Chapter 5 describes studies on the mP450-mediated oxidation of various eleuthoside structures obtained. Finally, Chapter 6 details the construction of an electrochemical flow cell, and its use for the anodic oxidation of furfuryl alcohol derivatives.
Supervisor: Robertson, Jeremy Sponsor: European Commission Seventh Framework Programme ; Cancer Research UK
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Chemistry ; Organic ; Diels-Alder reactions ; eleutherobin ; cytochrome P450 ; biocatalysis ; natural products