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dc.contributor.advisorWhite, Theodore
dc.contributor.authorKnudtson, Christopher A.
dc.date.issued2019
dc.date.submitted2019 Fall
dc.descriptionTitle from PDF of title page viewed January 14, 2020
dc.descriptionVita
dc.descriptionIncludes bibliographical references (page 252-253)
dc.descriptionThesis (Ph.D.)--Department of Chemistry, School of Pharmacy. University of Missouri--Kansas City, 2019
dc.descriptionDissertation advisor: Theodore White
dc.description.abstractIn Part I, the synthesis of chenodeoxychoic acid (CDCA) derivatives towards the construction of unique chemical architectures are reported. Building on previously described methods, CDCA based macrocycles with inner cavities have been synthesized and characterized. Attempts toward oxa-Michael coupling of CDCA monomers to form sulfonate ester linked dimmers is described. CDCA was also functionalized with terminal alkynes (pentynyl, hexynyl, and heptynyl) and aryl iodide and cyclized to from the respective macrocycles. These have been coupled together via oxygen-free Sonogashira reaction conditions to form large barrel-like steroidal architectures. These structures were investigated by 1H NMR, 13C NMR spectroscopy, and HR-MS, and MALDI-TOF spectroscopy. In part II a game to teach organic chemistry, ChemKarta was evaluated as a teaching tool. Analysis of an undergraduate class’s impressions of the game showed that Chemkarta was an easy to learn and enjoyable game, but the amount of information in the game could be overwhelming for some students. Furthermore, the modular nature of the game was demonstrated by developing new cards to fit into the examined card set, as well as additional card sets to teach different subjects using the same game rules.
dc.description.tableofcontentsIntroduction -- Literature review -- Oxa-Michael strategies toward CDCA dimers -- Synthesis of bile acids derivatives towards macrocycle construction via Sonogashara coupling -- Evaluation and expansion of Chemkarta -- Conclusion -- Appendix A. Functional groups -- Appendix B. Functional Groups Victory and Technique Cards --Appendix C. Structure and bonding -- Appendix D. Name reactions
dc.format.extentxiii, 316 pages
dc.identifier.urihttps://hdl.handle.net/10355/71050
dc.subject.lcshBile acids
dc.subject.lcshSteroids
dc.subject.lcshChemistry, Organic -- Study and teaching
dc.subject.otherDissertation -- University of Missouri--Kansas City -- Chemistry
dc.subject.otherDissertation -- University of Missouri--Kansas City -- Pharmacy
dc.titlePart I: Synthesis of functionalized bile acids towards the construction of steroidal macrocycles. Part II: Evaluation and expansion of a modular card game for teaching organic chemistry
thesis.degree.disciplineChemistry (UMKC)
thesis.degree.disciplinePharmaceutical Sciences (UMKC)
thesis.degree.grantorUniversity of Missouri--Kansas City
thesis.degree.levelPh.D.
thesis.degree.levelDoctoral
thesis.degree.namePh.D. (Doctor of Philosophy)


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