Studies Towards the Discovery of Antibacterial Natural Products and the Development of a Novel Ruthenium-Catalyzed Homo Diels-Alder [2+2+2] Cycloaddition

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Studies Towards the Discovery of Antibacterial Natural Products and the Development of a Novel Ruthenium-Catalyzed Homo Diels-Alder [2+2+2] Cycloaddition

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dc.contributor.advisor Tam, William
dc.contributor.author Kettles, Tanner James
dc.date 2012-04-10
dc.date.accessioned 2012-04-19T15:19:46Z
dc.date.available 2013-04-10T05:00:14Z
dc.date.issued 2012-04-19
dc.identifier.uri http://hdl.handle.net/10214/3507
dc.description.abstract The isolation and identification of the active constituents from an Allium sp. extract possessing antibacterial activity was undertaken. The plant material of interest was extracted, purified and screened for antibacterial activity against a Gram positive bacteria. Multiple trials were performed and the isolation was scaled-up repeatedly, overall three compounds potentially possess the observed activity. One compound was identified to yield the majority of activity, and a refined procedure for its purification was established. Initial characterization studies demonstrated the major isolate of interest is novel compared to other isolates from the Allium genus. A ruthenium-catalyzed homo Diels-Alder [2+2+2] cycloaddition between bicyclo[2.2.1]hepta-2,5-diene and alkynyl phosphonates was also studied. The observed reactivity was found to be dependent on the presence of the phosphonate moiety. The cycloaddition was compatible with a variety of aromatic and aliphatic substituted alkynyl phosphonates providing the corresponding phosphonate substituted deltacyclenes in low to good yields (up to 88%). en_US
dc.language.iso en en_US
dc.subject Natural products en_US
dc.subject Organic chemistry en_US
dc.subject Cycloadditions en_US
dc.subject Bicyclic alkenes en_US
dc.subject Allium isolation en_US
dc.subject homo Diels-Alder en_US
dc.subject [2+2+2] en_US
dc.subject Compound isolation en_US
dc.subject transition metal catalysis en_US
dc.title Studies Towards the Discovery of Antibacterial Natural Products and the Development of a Novel Ruthenium-Catalyzed Homo Diels-Alder [2+2+2] Cycloaddition en_US
dc.type Thesis en_US
dc.degree.programme Chemistry en_US
dc.degree.name Master of Science en_US
dc.degree.department Department of Chemistry en_US


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