Studies directed towards the total synthesis of (+)-peloruside A

dc.contributor.advisorPagenkopf, Brian L.en
dc.creatorEngers, Darren Williamen
dc.date.accessioned2008-08-28T22:53:53Zen
dc.date.available2008-08-28T22:53:53Zen
dc.date.issued2006en
dc.descriptiontexten
dc.description.abstractPeloruside A, isolated from marine sponge Mycale hentscheli, has shown potent cytotoxicity toward P388 murine leukemia cells (10 ng/mL, 18 nM), and functions like Taxol® by inducing apoptosis in the G2-M phase of the cell cycle through microtubulestabilization. To date, there have been two total synthesis of peloruside A. The goal of our research was to have the most efficient and practical synthesis of peloruside A. In this study, the application of a variety of aldol methodologies towards the convergent synthesis of peloruside A will be discussed. In our initial approach, the key synthetic strategy for peloruside A is the Mukaiyama aldol reaction between a glucosederived aldehyde and an α-benzyloxymethyl ketone. Alternatively, a similar segment of peloruside A can be constructed with a complex methyl ketone using a Walsh multicomponent coupling reaction and a Carreira enantioselective dienolate addition. The study is concluded with a concise synthesis of an advanced intermediate of peloruside A.
dc.description.departmentChemistry and Biochemistryen
dc.description.departmentChemistryen
dc.format.mediumelectronicen
dc.identifierb61298773en
dc.identifier.oclc72820918en
dc.identifier.urihttp://hdl.handle.net/2152/2530en
dc.language.isoengen
dc.rightsCopyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works.en
dc.subject.lcshAntimitotic agents--Synthesisen
dc.titleStudies directed towards the total synthesis of (+)-peloruside Aen
dc.type.genreThesisen
thesis.degree.departmentChemistryen
thesis.degree.disciplineChemistryen
thesis.degree.grantorThe University of Texas at Austinen
thesis.degree.levelDoctoralen
thesis.degree.nameDoctor of Philosophyen

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