Tags: Organic Seminar


Alkyne annulations: A toolkit for accessing chemical diversity from terpenoids to conjugated materials

Readily available alkyne-containing compounds are attractive as high-energy starting materials that allow an efficient, step- and atom-economical synthesis of a host of useful chemical products. Alkynes and polyynes can be used as linchpins in multicomponent and tandem reactions to provide rapid access to biologically pertinent terpenoid scaffolds. The alkyne functional group also allows for the facile synthesis of novel nanographenes and…


Transition Metal-Catalyzed Amination and Amidation Reactions

  Carbon–nitrogen bonds are ubiquitous in pharmaceuticals, organic materials, and natural products. These C–N bonds are often incorporated as amines or amides. Despite their prominence, they are often formed in poor atom and step economy. One of the primary goals of the Hull Group is to develop alternative syntheses of this two important functionalities. Our work towards chemo-, stereo-, and regioselective oxidative amidiation,…


Smart and Sweet Molecules: From Mannose to Self-Assembling Rods, Molecular Probes and Immunostimulatory Glycoclusters against Allergies and Cancer


Novel Applications of Photochemically Generated Quinone Methides and Naphthoquinone Methides in the Design of Metal Ion Chelators and Caged Fluorescent Dyes

Photochemical generation of o-naphthoquinone methides from 3-(hydroxymethyl)-2-naphthol derivatives (NQMPs) has been extensively studied by the research group of Dr. V. V. Popik.1-3 The application of NQMP-based photochemistry has been demonstrated on a variety of substrates. Thus, introduction of NQMP moiety into ion-selective chelators can be considered as a novel approach to control and change on-demand free ion metal concentration. We have…


Design, Synthesis and Biological Screening of NOX4 Inhibitors

NADPH oxidase (NOX) enzymes catalyze NADPH-dependent generation of reactive oxygen species and play a pivotal role in various physiological and pathological processes. Recent literature strongly suggests that NOX4 isoform plays a significant role in many disease states, such as fibrosis, cancers, and atherosclerosis. Thus, selective and potent inhibitors of NOX4 have the potential to be employed for the clinical management of a wide spectrum of…


Marine Biotoxins: Synthesis and Biological Impact


DNA-templated peptide fragments in mimicking protein-protein interactions


Diversely-Functionalized Oligonucleotides: Discovery of Modified DNA Aptamers and DNAzymes


Recent Efforts Toward Stereoselective Synthesis of Tetrasubstituted Olefins

Tetrasubstituted alkenes are a difficult functional group in organic synthesis to synthesize. The desire for stereoselective synthesis of tetrasubstituted alkenes has grown as well. Alkene synthesis can be divided into five categories of reactivity: Wittig-type, elimination, metathesis, additions across alkynes, and miscellaneous.  These reactions have a specific stereoselectivity that is seen in most cases. New methods for tetrasubstituted…


Recent Advances in o-Benzyne Chemistry: Aryne C¬–C Bond Insertions, Regioselective Syntheses with Benzdiyne Equivalents, and the Hexadehydro–Diels–Alder Reaction

Benzynes, as intermediates, have been known to chemists since the 1940’s through studies published by Wittig, Gilman, Horning, and Roberts.  The methods of generating this intermediate have evolved over time from using strong bases at low temperatures to milder conditions.  The most common method for generating o-benzyne is by the elimination of o-(trimethylsilyl) triflates with a fluoride anion source, the process of…
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