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EFFORTS TOWARDS THE SYNTHESIS OF SPIROLIGOZYMES AND PHOTOCHEMICAL METHODS FOR ACCESSING CYCLOBUTANOIDS AND CUBANE – LIKE COMPOUNDS
Fletcher, Steven Eugene-Scott
Fletcher, Steven Eugene-Scott
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Thesis/Dissertation
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2019
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Chemistry
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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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