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Development and Application of Protected Amino Acids for the Installation of Stable Post-translational Modifications Using Solid-Phase Peptide Synthesis
DownloadFall 2022
This thesis describes the synthesis of non-canonical amino acid building blocks and their use in solid-phase peptide synthesis (SPPS) to explore peptidic drug analogues based on natural products. We replaced sensitive functionalities found in the structure of naturally produced peptides with...
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Fall 2014
The five-membered carbocycle is a structural motif found in a plethora of natural products and bioactive compounds. The Nazarov reaction has emerged as an effective method to synthesize cyclopentenones and acts as a tool for adding structural complexity to molecular frameworks. This dissertation...
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Fall 2015
Organic chemistry has its foundations in the 19th century; since, it has grown into a number of industries affecting our daily lives such as the manufacture of goods and life saving pharmaceuticals. The need for new and increasingly efficient synthetic methods has grown in response to the...
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Seven- and Eight-Membered Ether Formation via Sulfonium Ylide Rearrangement Processes and Application in an Approach to (+)-Laurencin
DownloadSpring 2010
Given the large number of biologically active natural products containing medium-sized ether motifs, many organic chemists have shown great interest for developing new methodologies to access these structures. In particular, numerous synthetic methodologies for the construction of seven-membered...
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Synthesis, Structure and Properties of a Novel “Frustrated” Benzoxaborole and the Role of Boron in Bioconjugation
DownloadSpring 2020
Chapter 2 describes an optimized 7-step successful synthesis of a first of its kind permanently open-form ortho-hydroxyalkyl arylboronic acid, otherwise known as a “frustrated benzoxaborole”, with a columnless purification and complete structure elucidation. This novel compound is completely...
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Synthesis, structures and reactions of hydrotris(pyrazolyl)borate complexes of divalent and trivalent lanthanides
DownloadFall 2009
The synthesis and reactions of hydrotris(pyrazolyl)borate, (TpR,R′) supported ytterbium(II) borohydride and lanthanide(III) dialkyl (Ln = Yb, Lu) complexes were investigated. The lanthanide(III) dialkyl complexes were found to undergo both hydrogenolysis reaction and protonolysis reaction with...
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Fall 2011
The pradimicins are natural products that are both structurally intriguing to a synthetic chemist and possess biological activity as antifungal and antiviral agents. Our interest towards designing a synthetic route for these compounds and various analogues was sparked by the potential to produce...
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The Synthesis of and Methodology for Archipelago Model Asphaltenes with a Benzo[b]anthraquinoline Core
DownloadFall 2013
The efficient synthesis of model asphaltenes as polyaromatic, nitrogenous compounds is reported. These model asphaltenes are to be used for supramolecular investigation for developing enhanced bitumen processing methodology. Our synthesis of benzo[f]quinoline and benzo[b]anthraquinoline...
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Spring 2014
Fluorous phase chemistry is an emerging field in terms of new separation techniques. A highly fluorinated compound tends to dissolve in a fluorinated solvent rather than in a common organic solvent. Fluorophilic solid phase separation (F-SPE) techniques are also well established. Our goal is to...
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Tuning π-Conjugated Polymers with Heteroatoms: Synthesis of Polytellurophenes and Soluble Polyacetylenes
DownloadFall 2021
This Thesis describes the synthesis and investigation of π-conjugated oligomers and polymers with optoelectronic properties affected by the presence of a heteroatom. Two major classes of polymers are discussed: 1) polytellurophenes, where the backbone is formed by 5-membered heterocycles...