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dc.contributor.advisor Coltart, Don M en_US
dc.contributor.author Kohler, Mark Christopher en_US
dc.date.accessioned 2012-05-25T20:18:49Z
dc.date.available 2014-05-15T04:30:05Z
dc.date.issued 2012 en_US
dc.identifier.uri http://hdl.handle.net/10161/5546
dc.description Dissertation en_US
dc.description.abstract <p>This dissertation deals with the development of asymmetric carbon-carbon and carbon-heteroatom bond-forming reactions and the synthesis of Lagunamide A. Asymmetric C-C and C-X bond formations are critical transformations in synthetic chemistry. While a variety of approaches are available to effect such reactions, organocatalytic methods have attracted considerable recent attention. Common themes have emerged from these studies with regard to both the mode of asymmetric catalysis and the nature of the substrates they are applied to. We have been investigating alternatives to these themes for both carbon-carbon and carbon-heteroatom bond formation. We will describe some of our efforts to expand the parameters of asymmetric organocatalysis, which include the development a novel biomimetic proximity-assisted soft enolization approach to the asymmetric Mannich reaction, as well as the use of nitrosoalkenes for the asymmetric a-sulfenylation of ketones and aldehydes. Lagunamide A was recently isolated from Palau Hantu Besar, Singapore and has shown strong antimalarial activity and cytotoxicity against leukemia. The work presented describes the progress towards the first asymmetric total synthesis of this natural product.</p> en_US
dc.subject Organic chemistry en_US
dc.subject Asymmetric en_US
dc.subject Mannich en_US
dc.subject Natural Product en_US
dc.subject Nitrosoalkene en_US
dc.subject Sulfenylation en_US
dc.subject Thioester en_US
dc.title Part I: The Development of the Organocatalytic Asymmetric Mannich and Sulfenylation Reactions Part II: Progress Towards the Synthesis of Lagunamide A en_US
dc.type Dissertation en_US
dc.department Chemistry en_US
duke.embargo.months 24 en_US

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