dc.contributor.advisor | Harmata, Michael, 1959- | eng |
dc.contributor.author | Ying, Weijiang | eng |
dc.date.issued | 2009 | eng |
dc.date.submitted | 2009 Summer | eng |
dc.description | Vita. | eng |
dc.description | Title from PDF of title page (University of Missouri--Columbia, viewed on March 1, 2010). | eng |
dc.description | The 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.description | Dissertation advisor: Dr. Michael Harmata. | eng |
dc.description | Ph.D. University of Missouri--Columbia 2009 . | eng |
dc.description.abstract | [ACCESS RESTRICTED TO THE UNIVERSITY OF MISSOURI AT REQUEST OF AUTHOR.] 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.description.bibref | Includes bibliographical references. | eng |
dc.format.extent | xv, 430 pages | eng |
dc.identifier.oclc | 608241212 | eng |
dc.identifier.uri | https://hdl.handle.net/10355/6968 | |
dc.identifier.uri | https://doi.org/10.32469/10355/6968 | eng |
dc.language | English | eng |
dc.publisher | University of Missouri--Columbia | eng |
dc.relation.ispartofcommunity | University of Missouri--Columbia. Graduate School. Theses and Dissertations | eng |
dc.rights | Access is limited to the campus of the University of Missouri--Columbia. | eng |
dc.subject.lcsh | Chiral drugs | eng |
dc.subject.lcsh | Diastereoisomers | eng |
dc.subject.lcsh | Cyclobutane | eng |
dc.subject.lcsh | Benzothiazine | eng |
dc.subject.lcsh | Organic compounds -- Synthesis | eng |
dc.title | Study of the chemistry of 2,1-benzothiazines and toward the total synthesis of elisapterosin B | eng |
dc.type | Thesis | eng |
thesis.degree.discipline | Chemistry (MU) | eng |
thesis.degree.grantor | University of Missouri--Columbia | eng |
thesis.degree.level | Doctoral | eng |
thesis.degree.name | Ph. D. | eng |