Progress Toward the Synthesis of Apomorphine: Chiral Auxiliary Mediated Interception of an Intramolecularly Formed N-Acyl Iminium Ion

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dc.contributor.advisorDaniel L. Comins, Committee Chairen_US
dc.contributor.advisorSuzanne Purrington, Committee Memberen_US
dc.contributor.advisorCarl Bumgardner, Committee Memberen_US
dc.contributor.advisorJames K. Whitesell, Committee Memberen_US
dc.contributor.authorNuckols, Michel Christianen_US
dc.date.accessioned2010-04-02T18:58:23Z
dc.date.available2010-04-02T18:58:23Z
dc.date.issued2004-03-16en_US
dc.degree.disciplineChemistryen_US
dc.degree.leveldissertationen_US
dc.degree.namePhDen_US
dc.description.abstractGlaucine, which contains an aporphine skeleton, has been previously synthesized utilizing an intermolecular approach to form an iminium ion for the Pictet-Spengler reaction. A diastereomeric excess of 79% resulted as mediated by a chiral auxiliary. Progress was made in attempting to increase the diastereomeric excess by using an intramolecular approach to iminium ion formation. Apomorphine is a suitable platform on which to demonstrate the asymmetric interception of a chiral N-acyl iminium ion generated by intramolecular means. Several routes to this end were explored. These routes included the use of an intramolecular variant on the previously published work, Grubbs' metathesis and Horner-Wadsworth-Emmons among others. While no route proved successful in the end, understanding of the formation of aporphine skeletons was expanded upon.en_US
dc.identifier.otheretd-01292004-153110en_US
dc.identifier.urihttp://www.lib.ncsu.edu/resolver/1840.16/4654
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.subjectapomorphineen_US
dc.subjectiminium ionen_US
dc.subjectHorneren_US
dc.subjectchiral auxiliaryen_US
dc.subjectSuzukien_US
dc.titleProgress Toward the Synthesis of Apomorphine: Chiral Auxiliary Mediated Interception of an Intramolecularly Formed N-Acyl Iminium Ionen_US

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