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dc.contributor.advisorLawrence, Andrewen
dc.contributor.advisorLusby, Paulen
dc.contributor.authorDe Silvestro, Ireneen
dc.date.accessioned2018-04-18T08:38:52Z
dc.date.available2018-04-18T08:38:52Z
dc.date.issued2017-11-30
dc.identifier.urihttp://hdl.handle.net/1842/29575
dc.description.abstractThis thesis is regarded with the biomimetic total synthesis of phenolic natural products and describes two different projects. Chapter 1 introduces phenolic natural products, the most important biosynthetic pathways for their formation and some examples of relevant biomimetic syntheses. A short introduction to dimeric and pseudo-dimeric natural products can also be found in this chapter. Specific introductions can be found at the start of Chapters 2 and 3. Chapter 2 describes the total synthesis of a dimeric thymol derivative isolated from Arnica sachalinensis (which we have named “thymarnicol”). Inspired by the biosynthesis proposed by Passreiter and co-workers, we tested and confirmed the feasibility of a key hetero-Diels–Alder dimerisation step. During our investigations, we gained significant new insights into the origin and reactivity of thymarnicol. The final oxidative cyclisation has been found to occur spontaneously upon exposure to visible light in air. Chapter 3 discusses our efforts to develop a divergent biomimetic synthetic strategy towards a family of prenylated phenylpropanoid natural products isolated from Illicium genus plants. Our first biomimetic approach revealed the chemical instability of our proposed key intermediates. Therefore, a revised approach was trialled, allowing the total synthesis of a small set of natural products and related structures. We envisage that this strategy could be exploited by accessing a large number of members of this family of compounds.en
dc.language.isoen
dc.publisherThe University of Edinburghen
dc.relation.hasversionDe Silvestro, I.; Drew S. L.; Nichol G. S.; Duarte F.; Lawrence A. L., Angew. Chem. Int. Ed. 2017, 56, 6813. International Edition: DOI: 10.1002/anie.201701481en
dc.subjectbiomimetic synthesisen
dc.subjectbiosynthesisen
dc.subjectdimeric thymol derivativeen
dc.subjectArnica sachalinensisen
dc.subjectprenylated phenylpropanoiden
dc.titleTotal synthesis of phenolic natural productsen
dc.typeThesis or Dissertationen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD Doctor of Philosophyen


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