Tags: Organic Seminar


Triazole-Au(I) Catalysis: From stability to selectivity

Homogeneous gold catalysis has been developed explosively during the past decades.  Despite the remarkable electrophilic activation of alkynes by cationic Au(I) catalysts, such as PPh3Au+, one challenge is to overcome their poor stability at high temperature.  However, in order to activate some less reactive substrates, such as internal alkynes, harsher reaction conditions are usually required. As a good σ-donor and π-receptor,…


Decarboxylative Fluoroalkylation and Fluorination Strategies for Modulating Properties of Neurotherapeutics

Alcohols, ketones and aldehydes represent some of the most commonly exploited functional groups for synthetic transformations, and the extensive number of these motifs in natural products and pharmaceutically important building blocks provides a wide variety of potential substrates for transformations. In this field, we have developed new reactions and synthetic sequences using decarboxylative strategies and fluorinated alkenes to convert simple…


PROTEIN CARBOHYDRATE INTERACTIONS AND DISEASE

The recognition of carbohydrates by proteins is an important phenomenon in living systems and also plays a role in numerous diseases. Interference with these interactions is an important goal towards drug development. Interference is possible by multivalent carbohydrates that greatly enhance inhibitory potency compared to monovalent inhibitors. Bacterial lectins and toxins have been explored with the goal of optimizing inhibition by optimizing…


TOTAL SYNTHESIS OF PYRROLE IMIDAZOLE ALKALOIDS ENABLED BY A UNIQUE CHEMOSELECTIVE OXIDATION

Total Synthesis of Pyrrole Imidazole Alkaloids enabled by a Unique Chemoselective Oxidation The Axinellamines, Massadines, and Palau’amine are complex marine natural products belonging to the oroidin family isolated from sponge agelas oroides. Their complex structures, varying modes of functionalities, and biological activities have made them attractive targets for total synthesis. Although isolated in 1993, Palau’amine was not synthesized until…


Bioorthogonal Chemistry: SPAAC and Tetrazine Ligation


The Thiol-ene Reaction and Its Applications


Making DNA more Protein-like for Artificial DNA-Enzyme Discovery: Where Chemistry Meets Molecular Biology

Enzyme mimicry can provide fundamental insight into catalyst design as well new catalysts for therapy, sensing, and fine chemical transformations. Nucleic acid catalysts hold great promise as enzyme mimics yet lack many of the chemical functionalities commonly seen at the active sites of protein enzymes.  Since 1999, co-workers and I have worked to extend the catalytic potential of DNAzymes by incorporating modified dNTPs that are appended…


Chromium(III) Photooxidative Catalysis: Radical Cation Cycloadditions of Diazo Species and Alkenes


Microwave-Assisted Heterocyclic Compound Synthesis


Characterizing HMGA Binding to DNA and Inhibition by Small Molecules

HMGA (High Mobility Group Protein A) proteins are a family of nuclear proteins that bind AT rich DNA. These proteins are crucial during development and certain immune responses; however, their upregulation is linked to the spread of cancer. Unfortunately, the presence of HMGA1 (a subfamily of HMGA) is diagnostic of metastasis and poor prognosis for the patient. Therefore, downregulation of the DNA binding activity may allow for the development…
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