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Title: New applications of the 1,3-dipolar cycloaddition of pyrylium ylides in total synthesis
Author: Sloan , Colleen
Awarding Body: Queen's University Belfast
Current Institution: Queen's University Belfast
Date of Award: 2013
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The PhD project started with investigation of the 1,3-dipolar cycloadditions of pyrylim ylides with increasing level of substitution with a range of dipolarophiles. A library of complex 8- oxabicyclo[3,2,1]octanes was generated. During this study the conditions for the cycloaddition leading to formation of the central bi cyclic fragment of the anticancer natural product Englerin A were elaborated. This allowed synthesis of two simplified structural analogues of the natural product. Biological tests were performed in collaboration with Almac giving important information on the structure-activity relationship for this interesting kind of natural products. A pathway to the third more complex analogue was investigated and nearly brought to completion. Other branch of the investigation into the 1,3-dipolar cycloadditions of pyrylium ylides included stereoselective cycloadditions with chiral enamides leading to an asymmetric synthesis of a complex bicyclic amine. And the first example of the application of ball -milling for a solvent free 1,3-dipolar cycloaddition of pyrylium ylides was established .
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available