Browsing Faculty of Arts and Sciences by Keyword "Chemistry, Organic"
Now showing items 1-20 of 24
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A Platform for the Discovery of New Lincosamide Antibiotics
(2018-05-10)This dissertation presents a flexible synthetic approach to the lincosamide antibiotics, developed with the aim of rejuvenating an underexploited class to combat multidrug-resistant bacterial pathogens. The only clinically ... -
Activation of Electron-Deficient Quinones Through Hydrogen-Bond-Donor-Coupled Electron Transfer
(2015-09-23)Quinones are organic oxidants that play important roles in biological contexts and find wide application in organic synthesis. They are known to be activated toward electron transfer through hydrogen bonding, which has ... -
Activation of Weak Nucleophiles in Anion-Binding Catalysis
(2016-09-14)Anion-binding catalysis has emerged as a powerful principle for the development of highly enantioselective transformations. This strategy relies on the ability of dual hydrogen-bond donors to promote anion abstraction from ... -
Cooperative Asymmetric Catalysis with Squaramide H-Bond Donors and Lewis Acids
(2016-07-28)A new mode of cooperative catalysis with chiral squaramide hydrogen-bond donors and trialkylsilyl trifluoromethanesulfonates (triflates) for asymmetric nucleophilic additions to oxocarbenium ions was explored. Evidence is ... -
Development of Small Molecule Kinase Degraders as Chemical Biology Probes and Cancer Therapies
(2018-09-20)Advances in chemical biology provide immense benefits to human health through the discovery of new medicines and new scientific tools to study disease. I have contributed to the advancement of this field by developing a ... -
Engaging Chiral Cationic Intermediates by Anion-Binding in Asymmetric Catalysis
(2016-01-13)Anion-binding catalysis by dual hydrogen-bond donors such as ureas and squaramides has been demonstrated as a powerful strategy for the development of highly enantioselective transformations involving prochiral cationic ... -
I. Chiral Squaramide Catalysts for Lewis Acid Activation in Asymmetric Catalysis II. Catalytic, Stereoselective Difluorination Reactions
(2016-12-13)In Chapter 1, we report the observation that chiral squaramide hydrogen-bond (H-bond) donor catalysts act cooperatively with trialkylsilyl trifluoromethanesulfonates (silyl triflates) to promote enantioselective (4+3) ... -
I. Synthesis of C4-Modified Tetracyclines II. Aldolizations of Pseudoephenamine Glycinamide and Applications Toward the Synthesis of Monocyclic β-Lactam Antibiotics
(2015-05-14)Part one of this thesis describes the production of C4-modified tetracycline derivatives. Our synthetic strategy originally targeted SF2575, a C4-oxygenated tetracycline analog with antiproliferative properties, but was ... -
The Influence of Intramolecular Proton Relays on Catalysis
(2015-04-20)Global energy demand is predicted to increase at an alarming rate over the next century; in order to meet this demand while also limiting the effects of runaway climate change, society will need to shift toward renewable ... -
Investigations of the Biosynthesis and Structure of Colibactin, a Cytotoxin Made by Human-Associated Escherichia Coli
(2016-01-13)Humans exist in symbiosis with trillions of bacteria that are collectively referred to as the human microbiota. While commensal microbes are essential for health, some resident microbes can promote disease. Certain strains ... -
Late-Stage Fluorination With 19F− and 18F− via Concerted Nucleophilic Aromatic Substitution
(2016-09-09)The formation of C–F bonds has long been considered a challenging transformation and C–F bonds commonly had to be formed early on in a synthetic sequence towards complex organofluorides. Late-stage fluorination reactions ... -
Lessons From Cyclosporine A: Structural Determinants of Conformation-Switching and Passive Membrane Penetration
(2015-10-15)The structural complexity of ‘beyond-rule-of-5’ compounds, such as peptide macrocycles, may facilitate access to additional biological target space beyond the enzymatic active site. Naturally occurring cyclic peptides, in ... -
A Mechanistic Approach Towards Highly Efficient Anion-Binding Catalysts
(2016-09-14)Over the past decade, organocatalysis has emerged as a thriving area of research in the field of small-molecule asymmetric catalysis. In this context, the development of highly efficient catalysts—i.e. TON ≥ 1000, TOF ≥ ... -
Mechanistic Studies in Enantioselective Ion-Pairing Catalysis With Dual Hydrogen-Bond Donors
(2016-12-20)Enantioselective ion-pairing catalysis has emerged as a powerful strategy for controlling the stereochemical outcomes of reactions proceeding through charged intermediates. While ion pairing between chiral ionic catalysts ... -
Mechanistic Studies of First-Row Metal-Mediated and -Catalyzed Reactions
(2018-04-10)First-row transition metals find growing applications in organic transformations due to their abundance and low cost. In addition, the difference in redox states of first-row metals to those of second or third row metals ... -
New meta-Terphenyl-Derived Primary Amines in Asymmetric Catalysis
(2015-02-05)In this dissertation, two distinct asymmetric reaction types are described: [5 + 2] pyrylium cycloadditions and aldehyde α-functionalizations. Both reactions are mediated by simple, organic primary amine catalysts bearing ... -
Nonhydrolyzable Ribonucleotide Phosphoroimidazolide Analogues for Mechanistic Studies of Nonenzymatic RNA Replication
(2018-04-17)Efficient and faithful replication of genomic information is perhaps one of the most important hallmarks of cellular life. At some early point, such processes must have occurred in the absence of elaborate nucleic acid or ... -
On the Biological Activity of the Natural Product (+)-Avrainvillamide
(2015-05-07)Nucleophosmin (NPM1) is a multifunctional phosphoprotein localized predominantly within the nucleoli of eukaryotic cells. Mutations within its C-terminal domain are frequently observed in patients with acute myeloid leukemia ... -
Organic Molecule-based Electrolyte Materials for Aqueous Redox Flow Battery
(2017-08-31)Solar and wind energies have been growing so fast that in many regions around the world they have become the cheapest source for electricity production. Nevertheless, as we rely increasingly on solar and wind energies, one ... -
Palladium-Catalyzed Arene Functionalization via Single-Electron Reduction of Selectfluor
(2016-08-26)Palladium-catalysis is commonly used in the functionalization of aromatic rings, ranging from prefunctionalized substrates such as aryl metals or aryl (pseudo)halides to the direct functionalization of aromatic C–H bonds. ...