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Title: Approaches towards the synthesis of 1,1-Bis-hydroxymethyl-1,5-dideoxy-1,5-imino-L-fucitol
Author: Brown, David Tristram
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2001
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This thesis describes the design and testing of various strategies for the synthesis of the polyhydroxylated bis-hydroxylmethyl piperidine i, a component of a potential transition state inhibitor of an a-(1,3)-fucosyltransferase. (Fig. 16051A) The first chapter reviews the current methods by which complex piperidines are synthesised and outlines the aims of this project. The second chapter describes the attempted construction of an appropriate linear precursor for a nucleophilic cyclisation of an amine onto an epoxide. This chapter also describes an approach which attempted the electrophilic cyclisation of an alkene onto an imine, however an Aza-Cope [3,3]-sigmatropic shift took precedence. The third chapter describes attempts to construct the target via a catalytic aza-Diels-Alder reaction of an oxazinone. The fourth chapter describes an approach in which an inverse electron demand Diels-Alder reaction was used to establish the core stereochemistry. The piperidine ring was set up via a ring cleavage/reclosure method incorporating a Hofmann rearrangement and oxidative cleavage of an alkene. This method was used to synthesise the piperidine ii, however time constraints did not allow the extension of the approach beyond this test-case to the target i. (Fig. 16051B) It is proposed that a simple, efficient and adaptable methodology for the synthesis of this motif has been established.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available