Studies and synthetic applications of α-fluoro-α,β-disubstituted morpholine amides generated from acyl-Claisen rearrangements

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dc.contributor.advisor Barker, D en
dc.contributor.author Lo, Stephen en
dc.date.accessioned 2015-10-06T20:37:55Z en
dc.date.issued 2015 en
dc.identifier.citation 2015 en
dc.identifier.uri http://hdl.handle.net/2292/27159 en
dc.description Full text is available to authenticated members of The University of Auckland only. en
dc.description.abstract Tetrasubstituted tetrahydrofuran lignans are natural products which exhibit a host of biological activities and are potential candidates as drug compounds. Previously the total syntheses of a series of these lignans has employed the acyl-Claisen rearrangement as the key reaction to generate stereodefined compounds. This thesis describes the syntheses and studies of six novel α-fluoro-α,β-disubstituted morpholine amides 83 – 87 generated using an acyl-Claisen rearrangement process. These novel fluorinated amide compounds were characterized and compared to their non-fluorinated counterparts. A number of these amides were converted into 5-membered iodolactones 101a – 103a and comprehensively analysed using NMR techniques to determine that the stereochemistry of 2- and 3- substituents of the fluorinated amides are in a syn relationship. The applicability of the fluorinated amides in the syntheses of fluorinated analogues of tetrahydrofuran lignans was demonstrated through the conversion of amide 83 to precursor alcohol 108 using the same synthetic route towards the natural tetrahydrofuran lignan galbegin (4). en
dc.publisher ResearchSpace@Auckland en
dc.relation.ispartof Masters Thesis - University of Auckland en
dc.relation.isreferencedby UoA99264819613902091 en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. en
dc.rights Restricted Item. Available to authenticated members of The University of Auckland. en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.rights.uri http://creativecommons.org/licenses/by-nc-sa/3.0/nz/ en
dc.title Studies and synthetic applications of α-fluoro-α,β-disubstituted morpholine amides generated from acyl-Claisen rearrangements en
dc.type Thesis en
thesis.degree.discipline Chemistry en
thesis.degree.grantor The University of Auckland en
thesis.degree.level Masters en
dc.rights.holder Copyright: The Author en
pubs.elements-id 490208 en
pubs.record-created-at-source-date 2015-07-13 en


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