Synthetic Investigations towards the Total Synthesis of Neuroprotective Natural Products

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dc.contributor.advisor Brimble, M en
dc.contributor.advisor Sperry, J en
dc.contributor.advisor Furkert, D en
dc.contributor.author Wadsworth, Andrew en
dc.date.accessioned 2014-07-03T03:26:26Z en
dc.date.issued 2014 en
dc.identifier.citation 2014 en
dc.identifier.uri http://hdl.handle.net/2292/22392 en
dc.description.abstract This thesis describes synthetic work undertaken towards the synthesis of the neuroprotective natural products mescengricin (12), palmyrolide A (13) and sanctolide A (14). Investigations towards the synthesis of mescengricin (12) were initially directed towards cyclisation of diarylamines 175. Attempts were made to elaborate diarylamines 175 with a view to produce the tricyclic α-carboline core of 12 via cyclisation to form the central pyrrole ring. Difficulties effecting the cyclisation of 175 led us to further investigate the electronic properties of the diarylamines 175. Completion of an important model study led to the synthesis of simplified α-carboline (15) by employing the photocyclisation of diarylamine 167. The total synthesis of the macrocyclic N-methyl enamide palmyrolide A (13f) is next reported. This was achieved using of a unique ring closing metathesis (RCM)/olefin isomerisation methodology that installed the key tertiary enamide functionality. With the successful completion of the synthesis of palmyrolide A (13f) an analogous RCM/olefin isomerisation strategy was used to effect the synthesis of the related macrolide sanctolide A (14a). en
dc.publisher ResearchSpace@Auckland en
dc.relation.ispartof PhD Thesis - University of Auckland 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.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 Synthetic Investigations towards the Total Synthesis of Neuroprotective Natural Products en
dc.type Thesis en
thesis.degree.grantor The University of Auckland en
thesis.degree.level Doctoral en
thesis.degree.name PhD en
dc.rights.holder Copyright: The Author en
dc.rights.accessrights http://purl.org/eprint/accessRights/OpenAccess en
pubs.elements-id 445053 en
pubs.record-created-at-source-date 2014-07-03 en


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