(+)-Desoxoprosopinine: A Model for the Total Asymmetric Synthesis of Prosopis Alkaloids

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dc.contributor.advisorDaniel L. Comins, Chairen_US
dc.contributor.advisorSuzanne Purrington, Memberen_US
dc.contributor.advisorSamuel Levine, Memberen_US
dc.contributor.authorSandelier, Matthew J.en_US
dc.date.accessioned2010-04-02T18:05:52Z
dc.date.available2010-04-02T18:05:52Z
dc.date.issued1999-06-04en_US
dc.degree.disciplineChemistryen_US
dc.degree.levelMaster's Thesisen_US
dc.degree.nameMSen_US
dc.description.abstractThis work develops a general synthesis of the Prosopis africana alkaloids, using a chiral auxiliary-mediated process. Enantiopure N-acyldihydropyridones were produced and used as intermediates, targeting (+)-desoxoprosopinine as a synthetic model for those alkaloids. The orientation of all three stereocenters was highly controlled, with the synthesis of intermediate 75, just short of the target, in 7steps with a 13.8% overall yield.en_US
dc.identifier.otheretd-19990604-084333en_US
dc.identifier.urihttp://www.lib.ncsu.edu/resolver/1840.16/1654
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.title(+)-Desoxoprosopinine: A Model for the Total Asymmetric Synthesis of Prosopis Alkaloidsen_US

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