Chemoenzymatic routes to enantiopure hydroxytetrahydrofurans: muscarine and its analogues

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dc.contributor.advisor Maguire, Anita R. en
dc.contributor.advisor Mccarthy, Daniel G. en
dc.contributor.author Beecher, Denis
dc.date.accessioned 2016-09-08T09:07:52Z
dc.date.issued 2015
dc.date.submitted 2015
dc.identifier.citation Beecher, D. 2015. Chemoenzymatic routes to enantiopure hydroxytetrahydrofurans: muscarine and its analogues. PhD Thesis, University College Cork. en
dc.identifier.endpage 278 en
dc.identifier.uri http://hdl.handle.net/10468/3071
dc.description.abstract Muscarine was identified as an active principle of the poisonous mushroom Amanita muscaria over 170 years ago and has been identified as an agonist of acetylcholine. The synthesis of all stereoisomers of muscarine have been accomplished at this stage by chemical methods and the biological activity of these compounds tested. A number of synthetic routes to enantiomerically pure muscarine and its analogues have been published. In this work, we are focussed on the use of a novel biotransformation strategy to access these compounds. Asymmetric synthesis involves targeting a synthetic pathway leading to one enantiomer of a compound and biocatalysis is one strategy used in asymmetric synthesis. Chapter 1 consists of a review of the relevant literature pertaining to the synthesis and stereoselective transformations of 3-hydroxytetrahydrofuranss. A review of synthetic routes to these compounds is presented, with a particular focus on routes to the natural product muscarine and its analogues. Chapter 2 discusses the preparative routes to the 3-hydroxytetrahydrofurans via 3(2H)- furanones. Steps amongst which include Rh(II) mediate cyclisation and kinetic resolution via baker’s yeast mediated carbonyl reduction, resulting in enantioenriched 3- hydroxytetrahydrofuran derivatives. Finally, application of this methodology to the preparation of all four enantiomers of an analogue of desmethylmuscarine and the synthesis of epimuscarine is described. Chapter 3 consists of a detailed experimental section outlining the synthetic procedures employed. en
dc.description.sponsorship Irish Research Council (EMBARK initiative RS.2005.7) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher University College Cork en
dc.rights © 2015, Denis Beecher. en
dc.rights.uri http://creativecommons.org/licenses/by-nc-nd/3.0/ en
dc.subject 3(2H)-furanone en
dc.subject 3-hydroxytetrahydrofuran en
dc.subject Bakers' yeast en
dc.subject Muscarine en
dc.subject Desmethylmuscarine en
dc.subject Diazo en
dc.title Chemoenzymatic routes to enantiopure hydroxytetrahydrofurans: muscarine and its analogues en
dc.type Doctoral thesis en
dc.type.qualificationlevel Doctoral en
dc.type.qualificationname PhD (Science) en
dc.internal.availability Full text not available en
dc.check.info Restricted to everyone for five years en
dc.check.date 2021-09-07T09:07:52Z
dc.description.version Accepted Version
dc.contributor.funder Irish Research Council en
dc.contributor.funder University College Cork en
dc.description.status Not peer reviewed en
dc.internal.school Analytical and Biological Chemistry Research Facility en
dc.internal.school Chemistry en
dc.check.reason Releasing this thesis would cause substantial prejudice to the commercial interests of University College Cork en
dc.check.opt-out Not applicable en
dc.thesis.opt-out false
dc.check.entireThesis Entire Thesis Restricted
dc.check.embargoformat Both hard copy thesis and e-thesis en
ucc.workflow.supervisor a.maguire@ucc.ie
dc.internal.conferring Summer 2016 en


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