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dc.contributor.advisorHarmata, Michael, 1959-eng
dc.contributor.authorYing, Weijiangeng
dc.date.issued2009eng
dc.date.submitted2009 Summereng
dc.descriptionVita.eng
dc.descriptionTitle from PDF of title page (University of Missouri--Columbia, viewed on March 1, 2010).eng
dc.descriptionThe entire thesis text is included in the research.pdf file; the official abstract appears in the short.pdf file; a non-technical public abstract appears in the public.pdf file.eng
dc.descriptionDissertation advisor: Dr. Michael Harmata.eng
dc.descriptionDissertations, Academic -- University of Missouri--Columbia -- Chemistry.eng
dc.descriptionPh.D. University of Missouri--Columbia 2009 .eng
dc.descriptionIncludes bibliographical references.eng
dc.description.abstract[ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT AUTHOR'S REQUEST.] Using enantiomerically pure benzothiazines as templates, enantiomerically pure cyclobutanes were prepared. Such compounds are potentially interesting synthetic intermediates. The sequence developed for the preparation of these compounds, as well as some of their chemistry, is described. Treatment of certain benzothiazines bearing allylic bromides side chains with indium tribromide resulted in the formation of eight-membered rings in addition to the expected six-membered rings. Several attempts have been tried to approach the total synthesis of elisapterosin B, an important antitubercular and antimalarial marine natural product. Several methods have been tested: a diastereoselective intramolecular Friedel-Crafts alkylation reaction, an E-selective olefin cross-metathesis, and an asymmetric intermolecular Michael addition. A high diastereoselective methanesulfonic acid-catalyzed IFCA reaction of benzothiazine diene has been successfully used in total synthesis of pseudoteroxazole in the Harmata group. Seventeen benzothiazine dienes have been synthesized to study the factors that inference diastereoselectivity. Transition states were proposed and discussed. Protonation of benzothiazine was also studied via [superscript 1]H and [superscript 13]C NMR spectrum.eng
dc.format.extentxv, 430 pageseng
dc.identifier.oclc608241212eng
dc.identifier.urihttps://hdl.handle.net/10355/6968
dc.identifier.urihttps://doi.org/10.32469/10355/6968eng
dc.languageEnglisheng
dc.publisherUniversity of Missouri--Columbiaeng
dc.relation.ispartofcollectionUniversity of Missouri--Columbia. Graduate School. Theses and Dissertations.eng
dc.rightsAccess is limited to the campus of the University of Missouri--Columbia.eng
dc.subject.lcshChiral drugseng
dc.subject.lcshDiastereoisomerseng
dc.subject.lcshCyclobutaneeng
dc.subject.lcshBenzothiazineeng
dc.subject.lcshOrganic compounds -- Synthesiseng
dc.titleStudy of the chemistry of 2,1-benzothiazines and toward the total synthesis of elisapterosin Beng
dc.typeThesiseng
thesis.degree.disciplineChemistry (MU)eng
thesis.degree.grantorUniversity of Missouri--Columbiaeng
thesis.degree.levelDoctoraleng
thesis.degree.namePh. D.eng


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