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Graduate Theses and Dissertations

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Full-Text Articles in Organic Chemistry

Biorenewable Chemicals In Organic Synthesis: Applications Of Methyl Coumalate And Nitroquinones, Huangchao Yu Jan 2019

Biorenewable Chemicals In Organic Synthesis: Applications Of Methyl Coumalate And Nitroquinones, Huangchao Yu

Graduate Theses and Dissertations

Methyl coumalate is a bio-renewable material derived from malic acid. In the first chapter, we focused on the Diels-Alder reaction of methyl coumalate with a variety of dienophiles, including enamines, magnesium salts of indoles and hydroxyquinones. Some provided the bicyclic lactone intermediates, which could be further transformed into aromatic esters by acid/base catalyzed ring opening reactions. Others went through a Diels-Alder/retro Diels-Alder cascade and the carbon dioxide was extruded, affording the corresponding products. As a result, isophthalates, naphthalates and anthraquinone derivatives were successfully synthesized according to this strategy. The natural product Tomichaedin was also synthesized in over 40 ...


Molecularly Imprinted Nanoparticles (Minps) For Molecular Recognition And Bio-Mimetic Catalysis In Water, Md Arifuzzaman Jan 2019

Molecularly Imprinted Nanoparticles (Minps) For Molecular Recognition And Bio-Mimetic Catalysis In Water, Md Arifuzzaman

Graduate Theses and Dissertations

Water-soluble molecularly imprinted nanoparticles (MINPs) were produced easily by double cross-linking of surfactant micelles in the presence of suitable template molecules. The micellar surface could be modified with different groups to help the binding of guest molecules. The core could be tuned though usage of amide-containing surfactants that gave a layer of hydrogen-bonding groups in the interior. The location and the orientation of these surface and internal functional groups were important to the molecular recognition of MINPs as receptors.

It remains difficult to construct mimics of enzymatic active sites with accurately positioned catalytic groups and tunable selectivity for substrates. Artificial ...


Catalytic Alkene And Carbonyl Functionalization Reactions, Tanner Lee Metz Jan 2019

Catalytic Alkene And Carbonyl Functionalization Reactions, Tanner Lee Metz

Graduate Theses and Dissertations

This thesis presents the development of bismuth(III) triflate-promoted conjugate additions of electron-rich heteroarenes to ,-disubstituted enones, regioselective 1,6-additions of electron-rich heteroarenes to dienones, and 1,2-addition of nucleophilic heteroarenes to progesterone, 17-hydroxyprogesterone acetate and andrenosterone. Additionally, this dissertation describes the first examples of intermolecular alkene carboacylation triggered by amide CN bond activation.

Chapter II discusses the development of catalytic conjugate additions of heteroarenes to ,-disubstituted enones. Additions of a range of heteroarene nucleophiles, including furans, indoles, pyrroles, and thiophenes to a variety of ,-disubstituted enones occur to form heteroarylated all-carbon quaternary centers in up to 90 ...


Interrogation Of Protein Function With Peptidomimetics, Olapeju Bolarinwa Jul 2018

Interrogation Of Protein Function With Peptidomimetics, Olapeju Bolarinwa

Graduate Theses and Dissertations

Proteins can be described as the “machineries” responsible for almost all tasks in the levels of organizational complexity in multi-cellular organisms namely: the cells, tissues, organs and systems. Any disorder in the function of a protein at any of these levels could result in disease, and a study of protein function is critical to understanding the pathological features of the disease at the molecular level. A quick glance at these abundantly present proteins reveals two striking features: large diversity of biological function, and the variations in structural complexity, which varies from simple random coils, to turns and helices, and on ...


Synthesis Of Novel Agents For The Treatment Of Infectious And Neurodegenerative Diseases, Benjamin Joe Eduful Apr 2018

Synthesis Of Novel Agents For The Treatment Of Infectious And Neurodegenerative Diseases, Benjamin Joe Eduful

Graduate Theses and Dissertations

Infectious and neurodegenerative diseases continue to be a major concern worldwide. In spite of the great advances in drug therapy for treating various infectious and neurodegenerative diseases, there is still an urgent need for new and improved drugs due to increasing drug resistance among pathogens, emergence of new pathogens, ease of transmission of infections, ineffective available treatments, toxicity associated with current standard of care, aging populations and the lack of better alternative treatment options.

The first part of this manuscript (chapters 1 - 5) describes the synthesis of novel agents active against Leishmania donovani. According to the World Health Organization (WHO ...


Intramolecularly Enhanced Receptors With Unusual Binding And Molecularly Imprinted Nanoparticles As Nanoreactors And Sensors, Xiaoyu Xing Jan 2018

Intramolecularly Enhanced Receptors With Unusual Binding And Molecularly Imprinted Nanoparticles As Nanoreactors And Sensors, Xiaoyu Xing

Graduate Theses and Dissertations

The conformational flexibility of a receptor is usually considered unfavorable to binding, due to the entropy loss upon binding. Inspired by the biological receptor with intra-receptor secondary binding sites which can strengthen guest binding, two series of artificial receptors with similar structures were constructed: pseudo crown ethers with aromatic donor/acceptor groups and aromatic tweezer molecules with carboxylic acids. When the guest binding was weakened by the solvents, i.e., pseudo crown ethers bound with cations in polar solvents and aromatic tweezers bound with counterparts in non-polar solvents, intra-receptor interactions became stronger and contributed to the guest binding. The overall ...


Manipulating Push-Pull Systems To Probe Biology And Photochemistry, Andrea Thooft Jan 2018

Manipulating Push-Pull Systems To Probe Biology And Photochemistry, Andrea Thooft

Graduate Theses and Dissertations

Photochemistry and photophysics are two rapidly expanding areas in science. The first part of this dissertation looks at the synthesis of a new fluorescent probe based on the well-known fluorophore nitrobenzoxadiazole (NBD). We synthesized a new derivative using the nitrile functional group as the electron withdrawing group. Our results showed our fluorophore (CBD) displayed redder emission than the nitro counterpart, and an emission range that was similar to that of the sulfonamide containing derivatives. Additionally CBD displayed extensive solvatochromic properties: high quantum yield and bluer emissions in nonpolar solvents while low quantum yield and redder emissions as the solvent polarity ...


Investigating Degradation Pathways In Organic Solar Cell Materials, Satvik Shah Jan 2018

Investigating Degradation Pathways In Organic Solar Cell Materials, Satvik Shah

Graduate Theses and Dissertations

Thin film organic solar is a recent technology with tremendous potential – low cost materials, quicker manufacturing processes and synthetic tuning of organic materials to optimize material properties. Cell efficiencies > 12% have already been achieved. But the bottleneck problem this technology faces is instability. Performance of these cells degrades much faster than traditional solar cells. The degradation occurs on exposure to solar radiation, both through extrinsic ingress of moisture and oxygen as well as intrinsic degradation mechanisms.

One of the most common type of thin film organic cell with efficiency ~10% is PTB7:PCBM organic solar cell. Hence I have tried ...


Design And Application Of Porous Organic Frameworks For Recyclable, Heterogeneous, Transition-Metal Catalysis, Brian Schumacher Jan 2018

Design And Application Of Porous Organic Frameworks For Recyclable, Heterogeneous, Transition-Metal Catalysis, Brian Schumacher

Graduate Theses and Dissertations

In this thesis, heterogeneous frameworks are explored and examined for their use in recyclable catalysis. Specifically, metal-organic-frameworks (MOFs) and covalent-organic-frameworks (COFs) containing bidentate nitrogen ligands are pursued for their use in transition metal catalysis.

Palladium(II)-functionalized COF (Pd@TpBpy COF) is demonstrated as a recyclable, heterogeneous catalyst for palladium-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones to form ketone products containing all-carbon quaternary centers in aqueous 50 mM NaTFA as the reaction medium. A wide range of arylboronic acids are added to various β,β-disubstituted enones in moderate-to-high yields.

Pyridine oxazoline derivatives are designed and synthesized for ...


Tuning Of Environmental Probes, Paige Bouc Jan 2018

Tuning Of Environmental Probes, Paige Bouc

Graduate Theses and Dissertations

ABSTRACT

This thesis describes two projects focusing on (1) the investigation of benzoxadiazole chromophore and (2) new methods for solid phase microextraction.

This thesis investigates how the diazole ring in nitrobenzoxadiazole affects environmental sensitivity. We developed a novel synthesis of isobenzofurans using anthranilic acid derivatives. The use of benzyne and bioorthogonal chemistry is used to achieve our isobenzofuran derivatives.

This thesis will address two different ways in which to improve solid phase microextraction methods. By utilizing a novel cross linker and reverse addition fragmentation chain transfer (raft) polymerization we are able to control polymerization to give us more consistent polymers ...


Transition Metal-Catalyzed Alkene Hydroacylation And Carboacylation, Kevin Leon Vickerman Jan 2018

Transition Metal-Catalyzed Alkene Hydroacylation And Carboacylation, Kevin Leon Vickerman

Graduate Theses and Dissertations

This dissertation presents the development of new catalysts for enantioselective, rhodium-catalyzed alkene hydroacylation to form polycyclic heterocyclic ketones, the first examples of nickel-catalyzed alkene carboacylation via amide C−N bond activation, and the first examples of enantioselective, intermolecular palladium-catalyzed alkene carboacylation via ester C−O bond activation.

Chapter II describes the enantioselective synthesis of polycyclic nitrogen, oxygen, and sulfur heterocycles by rhodium-catalyzed intramolecular alkene hydroacylation. The intramolecular hydroacylation reactions generate 1,4-dihydrocyclopenta[b]indol-3(2H)- ones and 3,4-dihydrocyclopenta[b]indol-1(2H)-one in moderate-to-high yields (65-99%) with good-to-excellent enantioselectivities (84-99% ee). The catalyst system also promotes alkene hydroacylation of ...


Design And Synthesis Of Cpg-Lytic Peptide Conjugate, Brachytherapy Beads And A Combinatorial Library Of Primary Amines Used As Potential Therapeutics In The Treatment Of Cancers, Josanne-Dee Woodroffe Nov 2017

Design And Synthesis Of Cpg-Lytic Peptide Conjugate, Brachytherapy Beads And A Combinatorial Library Of Primary Amines Used As Potential Therapeutics In The Treatment Of Cancers, Josanne-Dee Woodroffe

Graduate Theses and Dissertations

Cancer remains one of the most feared diseases affecting the modern world. Second to heart disease, it is the largest cause of deaths, affecting one in three persons. Cancer cells are formed when normal, healthy cells become damage, losing their normal regulatory mechanism that control cell growth. There are many different types and progression of these cancer cells that determine the type of treatment a patient receives. The primary focus of this dissertation is to propose three studies of anticancer agents. In Chapter one, a CpG-lytic peptide conjugate was designed to target receptors on the cell membrane to concentrate the ...


Formation Of Carbon-Carbon And Carbon-Hetero Bonds Through Gold Catalysis, Boliang Dong Oct 2017

Formation Of Carbon-Carbon And Carbon-Hetero Bonds Through Gold Catalysis, Boliang Dong

Graduate Theses and Dissertations

This dissertation mainly contains two parts: one is C-X (C, O, S) bond formation through gold(I) catalysis, one is new applications via gold(I/III) redox catalysis.

In first part, gold(I) catalysts would be introduced and their general applications, then the TA-Au species will be emphasized including the design, synthesis, characters and their application in catalysis. The applications are well developed during the past decade in our group, but here only involves three examples regarding C-C, C-O and C-S bond formations. From these effective applications, the unique stability and reactivity of TA-Au will be studied and explained, which ...


Synthesis, In Vitro Characterization And Applications Of Novel 8-Aminoquinoline Fluorescent Probes, Adonis Mcqueen Oct 2017

Synthesis, In Vitro Characterization And Applications Of Novel 8-Aminoquinoline Fluorescent Probes, Adonis Mcqueen

Graduate Theses and Dissertations

Malaria is a parasitic disease that is caused by the plasmodium parasite. Plasmodium infection has affected man for thousands of years. With advances in drug discovery over the past century, malaria has evolved to possess resistance to most mainline therapeutics. This war of drug discovery vs plasmodium evolution continues to be fought to this very day, with attempts to eradicate malaria worldwide. Frontline treatments such as chloroquine, artemisinin, and atovaquone/proguanil have all seen parasitic resistance in strains of P. vivax as well as P. falciparum. While plasmodium possesses resistance to most classes of anti-malarials, the 8-aminoquinoline (8-AQ) class has ...


New Reaction Discoveries In Gold Catalysis, Seyedmorteza Hosseyni Mar 2017

New Reaction Discoveries In Gold Catalysis, Seyedmorteza Hosseyni

Graduate Theses and Dissertations

In this dissertation, gold catalyst was employed to catalyze intermolecular reactions. Intramolecular reactions were far more advanced than intermolecular reaction in gold catalysis. With finding suitable ligands for gold catalysts, we were able to develop several transformations to synthesize interesting building blocks in organic chemistry including: allenes, furans, spiros, oxepines, propargyl ethers and ketones. These functionalities were synthesized by the use of triazole-gold(I) catalyst. Triazole, as a ligand bond to gold, showed enhanced stability of the catalyst, which resulted in better yields. Gold(I)/(III) redox chemistry also used for cyclopropanol ring openings which resulted in synthesizing substituted ketones.


Syntheses Of Natural Products And Molecules For Rna Imaging, Ivan M. Geraskin Jan 2017

Syntheses Of Natural Products And Molecules For Rna Imaging, Ivan M. Geraskin

Graduate Theses and Dissertations

The synthesis of natural products and biologically active molecules is one of the main applications of organic chemistry. Many natural products with valuable biological properties have low abundance in natural sources. Therefore, they need to be synthesized in sufficient quantities that their properties and activities can be studied. Chapter 1 describes synthesis of a library of biologically active compounds which are currently used in RNA imaging studies. Chapter 2 describes the synthesis of the procyanidin A skeleton. Procyanidins are important natural products with various biological activities. Chapter 3 describes a method for the preparation of anthocyanidins, natural products which possess ...


Total Synthesis And Characterization Of Breitfussins A And B, Akbar Husain Khan Jan 2017

Total Synthesis And Characterization Of Breitfussins A And B, Akbar Husain Khan

Graduate Theses and Dissertations

The breitfussins are highly modified halogenated marine alkaloids, containing an unprecedented indole-oxazole-pyrrole structure and breitfussin A is only known iodo-oxazole containing the natural product. Due to lack of enough information from conventional tools like NMR, mass spectroscopy, and IR, their structures were determined by an unusual application of atomic-force microscopy (AFM) along with other computational tools.

In the absence of selective halogenation on oxazole-pyrrole containing a molecular frame, the site-selective halogenation was studied on the model compound of breitfussins. It has been found that the oxazole and pyrrole rings proved to be comparably reactive towards electrophilic halogenation by N-chlorosuccinimide (NCS ...


Methods For Alkene Difunctionalizations: Hydroacylation & Carboacylation, James Alfonzo Walker Jr. Jan 2017

Methods For Alkene Difunctionalizations: Hydroacylation & Carboacylation, James Alfonzo Walker Jr.

Graduate Theses and Dissertations

This thesis presents the development of new catalyst for the coupling of alkene hydroacylation and enantioselective α-arylation to form heterocyclic ketones containing α-chiral quarternary stereocenters, the N-heterocyclic carbene-catalyzed intramolecular hydroacylation to form basic nitrogen-containing heterocycles, and the first examples of nickel-catalyzed alkene carboacylation triggered by amide C-N bond activation.

Chapter II discusses a strategy that combines alkene hydroacylation and enantioselective α-arylation to form a wide variety of nitrogen-containing heterocyclic ketones bearing α-chiral quarternary stereogenic centers. Exo-selective, intramolecular Ni-catalyzed hydroacylations of N-homoallylindole- and N-homoallylpyrrole-2-carboxaldehydes form α-substituted six-membered heterocyclic ketones in up to 95% yield, while N-heterocyclic carbene (NHC) catalyzed hydroacylations of ...


Enantioselective Synthesis Of Compounds Containing Bis-Benzylic Quaternary Stereocenters Through Palladium-Catalyzed Conjugate Additions Of Arylboronic Acids, Abhishek Ashok Kadam Jan 2017

Enantioselective Synthesis Of Compounds Containing Bis-Benzylic Quaternary Stereocenters Through Palladium-Catalyzed Conjugate Additions Of Arylboronic Acids, Abhishek Ashok Kadam

Graduate Theses and Dissertations

This thesis describes development of a catalyst system that allows formation of compounds containing bis-benzylic quaternary stereocenters. The work presented herein describes studies towards development of enantioselective, palladium-catalyzed conjugate additions of arylboronic acids to β-aryl, β,β-disubstituted enones to generate ketones containing bis-benzylic quaternary stereocenters. A catalyst generated in situ from palladium trifluoroacetate and a chiral, non-racemic (S)-4-tert-butyl-2-(2-pyridyl)oxazoline ligand ((S)-t-BuPyOx) promotes conjugate additions of a wide range of electronically and structurally diverse arylboronic acids to a variety of β-aryl, β,β-disubstituted enones. In this work, we have used iterative addition of the arylboronic acids as a ...


Asymmetric Transformations Catalyzed By Chiral Binol Alkaline Earth Metal Phosphate Complexes, Sri Krishna Nimmagadda Oct 2016

Asymmetric Transformations Catalyzed By Chiral Binol Alkaline Earth Metal Phosphate Complexes, Sri Krishna Nimmagadda

Graduate Theses and Dissertations

Small molecule hydrogen bond donors have emerged as versatile catalysts in asymmetric synthesis. Within this class, chiral BINOL phosphoric acid is regarded as one of the pioneer catalysts used in several asymmetric transformations. The ability of the catalyst to activate the substrates could be controlled in two different ways. (1) Dual activation/bifunctional activation of substrate by hydrogen bond interactions or ion pairing with phosphoric acid or (2) By forming chiral BINOL phosphate metal complex that could significantly alter the interactions in chiral space. In particular, chiral alkaline earth metal phosphate complexes have unique advantages as catalysts owing to the ...


Design And Development Of Peptidomimetic Ligands For Targeting Radiopharmaceuticals, Imaging Probes, And Immunotherapeutics In Oncologic Disease, Michael Lawrence Doligalski Oct 2016

Design And Development Of Peptidomimetic Ligands For Targeting Radiopharmaceuticals, Imaging Probes, And Immunotherapeutics In Oncologic Disease, Michael Lawrence Doligalski

Graduate Theses and Dissertations

Cancer is a leading cause of morbidity and mortality in the developed world. While much has been learned about these diseases in the last few decades, one of the main barriers to widespread advancement is the heterogeneity of cancer biology. A growing body of evidence supports the idea that certain protein receptors are overexpressed on the surface of tumor cells as compared to normal tissues. These extracellular biomarkers provide a unique opportunity to selectively target the tumor with both imaging and therapeutic modalities. The research in this dissertation focuses on targeting proteins on the tumor cell surface with peptidomimetic ligands ...


Spatially Directional Resorcin[4]Arene Cavitand Glycoconjugates For Organic Catalysis In Aqueous Media, Ali Husain Husain Jun 2016

Spatially Directional Resorcin[4]Arene Cavitand Glycoconjugates For Organic Catalysis In Aqueous Media, Ali Husain Husain

Graduate Theses and Dissertations

Resorcin[4]arenes and their rigid structures “cavitands” offer a unique molecular structure scaffolds suitable for attaching and orienting multi-ligands on their upper rims. Their remarkable structure properties, the relative ease of chemical modification on their either rims or through the multiple phenolic hydroxyl (-OH) groups, manipulating their cavity size and the role of spatial directionality provided by their cores, led synthetic chemist to explore their utilities in the synthesis of valuable resorcin[4]arene/cavitand assemblies with wide range of applications in many research areas such as supramolecular chemistry, host-guest chemistry, glycoconjugates, polymer chemistry, host-guest chemistry, micro-reactors in chemical ...


Co(Ii)-Based Metalloradical Catalysis For Asymmetric Radical Cyclopropanation, Qigan Cheng Apr 2016

Co(Ii)-Based Metalloradical Catalysis For Asymmetric Radical Cyclopropanation, Qigan Cheng

Graduate Theses and Dissertations

Metal-catalyzed cyclopropanation of olefins with diazo reagents is one of the most general and efficient method to prepare cyclopropanes. The resulting cyclopropyl units are found as a basic structural element in a wide range of naturally occurring compounds and biologically active compounds, and can serve as versatile synthetic intermediates in the synthesis of multifunctionalized cycloalkanes and acyclic compounds. Since Co(II) complexes of D2-symmetric chiral amidoporphyrins [Co(D2-Por*)] were first introduced in 2004, Co(II)-metalloradical catalysis (MRC) have emerged as a new platform for asymmetric cyclopropanation. These metalloradical catalysts have been shown to be highly ...


Enhancement Of Supercapacitor Energy Storage By Leakage Reduction And Electrode Modification, Tete Tevi Mar 2016

Enhancement Of Supercapacitor Energy Storage By Leakage Reduction And Electrode Modification, Tete Tevi

Graduate Theses and Dissertations

Supercapacitors have emerged in recent years as a promising energy storage technology. The main mechanism of energy storage is based on electrostatic separation of charges in a region at the electrode-electrolyte interface called double layer. Various electrode materials including carbon and conducting polymers have been used in supercapacitors. Also, supercapacitors offer high life cycle and high power density among electrochemical energy storage devices. Despite their interesting features, supercapacitors present some disadvantages that limit their competitivity with other storage devices in some applications. One of those drawbacks is high self-discharge or leakage. The leakage occurs when electrons cross the double layer ...


Chemical Investigation Of Antarctic Marine Organisms & Their Role In Modern Drug Discovery, Jacqueline Lee Fries Feb 2016

Chemical Investigation Of Antarctic Marine Organisms & Their Role In Modern Drug Discovery, Jacqueline Lee Fries

Graduate Theses and Dissertations

The chemicals produced by biological systems, whether proteins, peptides, or terpenes, will always provide an intriguing topic for researchers. Invisibly controlling every aspect of nature, these molecules are responsible for life, evolution, and death. Specifically, here is described the secondary metabolites produced by Antarctic marine organisms as well as others, and how they are used to defend or attract other animals while potentially providing health benefits to mankind. This is done through collection, extraction, and separation of individual specimens. The respective mixtures of compounds after isolation are then analyzed via spectroscopic methods such as nuclear magnetic resonance spectroscopy, mass spectrometry ...


Catalytic Methods For The Synthesis Of Spirooxindoles, Pyrroloindolines, And Flavanones, Anthony Gerten Jan 2016

Catalytic Methods For The Synthesis Of Spirooxindoles, Pyrroloindolines, And Flavanones, Anthony Gerten

Graduate Theses and Dissertations

This thesis discloses catalytic, enantioselective dipolar cycloadditions to deliver new nitrogen-containing heterocycles and formal hydroarylations of olefins that have previously not been possible.

Catalytic, enantioselective, dearomative cycloadditions of stabilized, α-substituted azomethine ylides with 3-nitroindoles occur in the presence of a catalytic complex generated from Cu(OTf)2 and (R)-Difluorphos. These reactions set four contiguous stereocenters, two of which are fully substituted. Overcoming the barrier of breaking aromaticity, this catalyst system delivers pyrrolo[3, 4b]indoles with exo´-selectivity in moderate-to-good yields (39-85%) with high diastereoselectivity (up to 98 : 1 : 1 dr) and enantioselectivity (up to 96% ee).

Catalytic ...


Synthesis And Conformational Analysis Of 2,2,6,6-Tetramethyl Piperdine Masked 1,2- Diols: Synthesis Of Oxylipins From Dracontium Lortense, Shreyosree Chatterjee Jan 2016

Synthesis And Conformational Analysis Of 2,2,6,6-Tetramethyl Piperdine Masked 1,2- Diols: Synthesis Of Oxylipins From Dracontium Lortense, Shreyosree Chatterjee

Graduate Theses and Dissertations

Various natural products have been isolated with promising bioactivities but in very small quantities, impeding structure elucidation and structure activity relationship studies. Therefore, synthesis of such natural products in laboratory becomes very important for structure determination and biological studies. Two isomeric oxylipins (a trihydroxy fatty acid) were isolated from the Peruvian plant Dracontium lortense in very minute quantities (1 mg of each). One of the oxylipins have shown promising activity as an immunostimulant. Although the relative stereochemistry of the natural product was assigned, due to scarcity the absolute configuration was unknown. The current work describes the synthesis and structural assignment ...


Transition Metal-Catalyzed Alkene Hydroacylation As A Platform For Enantioselective Synthesis Of Polycyclic Nitrogen Heterocycles, Avipsa Ghosh Jan 2016

Transition Metal-Catalyzed Alkene Hydroacylation As A Platform For Enantioselective Synthesis Of Polycyclic Nitrogen Heterocycles, Avipsa Ghosh

Graduate Theses and Dissertations

The prevalence of nitrogen heterocycles in medicinally important compounds has, for years, inspired synthetic chemists for developing strategies to form new heterocyclic scaffolds and methods that streamline the syntheses of complex heterocycles. Giving into the cause, this dissertation primarily focuses on development of transition-metal catalyzed hydroacylation of alkenes as a platform for enantioselective synthesis of multiple classes of polycyclic nitrogen heterocycles.

Development of catalytic, enantioselective intramolecular hydroacylation of N-vinylindole-2-carboxaldehydes that occur in the presence of a readily accessible rhodium catalyst and form chiral, non-racemic 2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-ones in high yields and enantioselectivities has been described. The dihydropyrroloindolone products ...


Synthesis Of Natural Product Analogs As Small Molecule Inhibitors, Pengfei Dong Jan 2016

Synthesis Of Natural Product Analogs As Small Molecule Inhibitors, Pengfei Dong

Graduate Theses and Dissertations

ABSTRACT

Natural products with interesting unique structures and special biological activities possess great potential in the development of novel pharmaceuticals. However, the evaluation of biological activity is always limited due to the low yield and difficulty of separation from plants and microorganisms. Synthetic organic chemistry provides an alternative tool to create such natural products from accessible materials. A huge mission for organic chemists is to develop novel strategies to produce natural products and their analogs in lab, as well as in quantitative scales. With this in mind, we have designed small molecule inhibitors towards Porcine reproductive and respiratory syndrome virus ...


Catalytic Enantioselective Α,Β,Γ-Trioxygenation And Anti-1,2-Diol From Α-Oxyaldehydes And Its Application In Total Synthesis Of Oxylipins Isolated From Dracontium Loretense, Gayan Aruna Abeykoon Jan 2016

Catalytic Enantioselective Α,Β,Γ-Trioxygenation And Anti-1,2-Diol From Α-Oxyaldehydes And Its Application In Total Synthesis Of Oxylipins Isolated From Dracontium Loretense, Gayan Aruna Abeykoon

Graduate Theses and Dissertations

Mother nature creates structurally diverse interesting secondary metabolites often with unexpected biological activity, but in scarce quantities. Target-oriented total synthesis provides access to such natural products in sufficient amounts for further exploration of bioactivity. In target-oriented total synthesis, there is a never ending demand for the development of new reaction methodologies in order to address challenges in the synthesis and also to improve current synthetic protocols. Taking this idea to heart, we have worked on novel asymmetric method development and applied some of the methodologies that we developed to total synthesis. This thesis is composed of five chapters. Chapter 1 ...