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    EFFORTS TOWARDS THE SYNTHESIS OF SPIROLIGOZYMES AND PHOTOCHEMICAL METHODS FOR ACCESSING CYCLOBUTANOIDS AND CUBANE – LIKE COMPOUNDS

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    Genre
    Thesis/Dissertation
    Date
    2019
    Author
    Fletcher, Steven Eugene-Scott
    Advisor
    Sieburth, Scott McNeill
    Committee member
    Fleming, Steven A. (Steven Alan)
    Wengryniuk, Sarah E.
    Martinez Solorio, Dionicio
    Department
    Chemistry
    Subject
    Chemistry, Organic
    Teacher Education
    Permanent link to this record
    http://hdl.handle.net/20.500.12613/2866
    
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    DOI
    http://dx.doi.org/10.34944/dspace/2848
    Abstract
    This work describes the culmination of two separate projects. In the first endeavor, efforts to synthesize peptidomimetics are described using trans-hydroxy proline to make a functionalized bis-peptides, or spiroligomers. The bis- peptide was then tested for catalytic activity on esterification reactions. The remainder of this manuscript describes a method to create complex molecular scaffolds using [4 + 4] photocycloaddition of trimethylsilyl substituted benzyl ethers tethered to 2 – pyridones. Upon irradiation at low concentrations, these structures intramolecularly react to give cyclobutanoid compounds. Initially, it was thought that [4 +4] photoreactions would would yield cyclooctanoid structures. Finally, a meta substituted methyl ester is intramoleculary reacted with a benzyl pyridone and eventually transformed into a dimethyl alcohol, creating a cubane – like structure. This caged structure is then subjected to rearrangement when exposed to strong acid conditions.
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