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Title: Diversity-Oriented Synthesis of Alkaloid-like Unnatural Products
Author: Leach, Stuart Grahame
ISNI:       0000 0001 3606 5197
Awarding Body: University of Leeds
Current Institution: University of Leeds
Date of Award: 2008
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This thesis describes the development of a novel methodology to allow the synthesis of skeletally diverse alkaloid-like unnatural compounds. Enantiomerically enriched building blocks are iteratively assembled onto a purification handle using reliable coupling reactions. Subsequently, ring-opening-ring-closing metathesis cascade reactions are used as a complexity generating step to restitch the molecular framework. Chapter 1 introduces the concept of diversity-oriented synthesis, with particular emphasis on strategies used to introduce skeletal diversity. The conceptual idea behind the project is explained, and placed into context using leading examples as the benchmark for success in diversity-oriented synthesis. Chapter 2 describes the synthesis of a range of building blocks, many of which are enantiomerically enriched, on multigram scale. The design of a solid phase 'linker' is described in Chapter 3, as are the solution phase studies used to explore suitable methodologies to couple the building blocks. The use of solid phase chemistry is described in Chapter 4, as well as the use of light fluorous tags as an alternative purification handle. Chapter 5 describes the synthesis and subsequent metathesis of a range of fluorous-tagged metathesis substrates using one building block iteration. The Thesis concludes with the preparation of 45 metathesis precursors using combinations of two building blocks assembled onto a fluoroustagged linker in Chapter 6. Metathesis cascades were carried out, allowing the isolation of 33 complex and skeletally diverse products.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available