Catalyst Design for Asymmetric Organozinc Addition to Aldehydes and Progress Toward the Total Synthesis of the Marine Alkaloid, (-)-Lepadiformine.

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dc.contributor.advisorDaniel L. Comins, Committee Chairen_US
dc.contributor.advisorChristian Melander, Committee Memberen_US
dc.contributor.advisorSuzanne T. Purrington, Committee Memberen_US
dc.contributor.advisorT. Brent Gunnoe, Committee Memberen_US
dc.contributor.authorMarks, Lucas Richarden_US
dc.date.accessioned2010-04-02T19:12:16Z
dc.date.available2010-04-02T19:12:16Z
dc.date.issued2006-05-10en_US
dc.degree.disciplineChemistryen_US
dc.degree.leveldissertationen_US
dc.degree.nameEdDen_US
dc.description.abstractA novel dihydropyridone was synthesized in search for a chiral ligand for the asymmetric addition of an alkyl group to an aldehyde. The target amine was derived from an enamine through a hydrogenation reaction. A study directed toward the total synthesis of the marine alkaloid (-)-lepadiformine was carried out. Two approaches were investigated toward the core perhydroquinoline system. The first approach utilized a Grignard addition to an N-acylpyridinium salt and a [2+2] photochemical addition as the key synthetic steps. The second approach was based upon quinoline chemistry. The model study was completed with a one-carbon alkene homologation to form a terminal butane. An asymmetric route was examined.en_US
dc.identifier.otheretd-04272006-085949en_US
dc.identifier.urihttp://www.lib.ncsu.edu/resolver/1840.16/5357
dc.rightsI hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dissertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to NC State University or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report.en_US
dc.subjectalkaloidsen_US
dc.subjectperhydorqunolineen_US
dc.subjectdihydropyridoneen_US
dc.subjectLepadiformineen_US
dc.titleCatalyst Design for Asymmetric Organozinc Addition to Aldehydes and Progress Toward the Total Synthesis of the Marine Alkaloid, (-)-Lepadiformine.en_US

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