Sieburth, Scott McNeill2020-11-042020-11-042019http://hdl.handle.net/20.500.12613/2866This 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.144 pagesengIN COPYRIGHT- This Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available.http://rightsstatements.org/vocab/InC/1.0/Chemistry, OrganicTeacher EducationText