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Title: Chemoenzymatic approches to cyclohexane based natural products
Author: Graham, Isla Patricia
ISNI:       0000 0001 3509 5765
Awarding Body: Queen's University Belfast
Current Institution: Queen's University Belfast
Date of Award: 2008
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Chapter 1 provides an overview of cis-dihydrodiols. The biological aspects of enzymatic hydroxylation are discussed, followed by the important stereochemical aspects of cis-diol metabolites. A selection of chemoenzymatic approaches to important natural products from cis-dihydrodiols is given. Chapter 2 introduces the Amaryllidaceae and Sceletium alkaloids, giving an insight into their biological sigIJificance. Previous approaches to important members of both alkaloid classes are given. Synthesis of a ke~ intermediate for the synthesis of mesembranol is described. The development of successful conditions to effect a Suzuki reaction of cis-dihydrodiols forms a key component of the synthetic strategy. Following on from this, Diels-Alder reactions of substrates derived from cisdihydrodiols, studies towards a resolving agent and biotransformation studies are discussed. Chapter 3 is devoted to synthesis of cis-3a-aryloctahydroindole nuclei, common to many Amaryllidaceae alkaloids. Previous approaches followed by our synthetic endeavours to gain access to this nucleus from cis-dihydrodiols are outlined. Chapter 4 begins with an introduction to 2-deoxystreptamine, an important aminocyclitol. Previous approaches to 2-deoxystreptamine are discussed. An important intermediate in several synthe~es is identified, followed by approaches to it from cis-dihydrodiols. The second half of the chapter is concerned with synthesis of valeinamine. Synthesis of a 3,4-trans-diol from iodobenzene-cis-diol is outlined. Chapter 5 contains full experimental details, including spectral and analytical data, for the compounds synthesised during this work.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available