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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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Title: Studies Towards the Discovery of Antibacterial Natural Products and the Development of a Novel Ruthenium-Catalyzed Homo Diels-Alder [2+2+2] Cycloaddition
Author: Kettles, Tanner James
Department: Department of Chemistry
Program: Chemistry
Advisor: Tam, William
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%).
URI: http://hdl.handle.net/10214/3507
Date: 2012-03
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