Tags: Organic Seminar


Synthesis, Evaluation, Mechanistic Studies of Thiasugars and Their Dithia Derivatives for Application in Medicinal and Bioorganic Chemistry

Thioglycosides and thiasugars both have a long history in bioorganic and medicinal chemistry 1-7 but it is widely considered that they are less “active” than the parent sugars. In our research, we sought to rationalize an application of thioglycosides, thiasugar glycosides, and their dithia-analogs in bio-organic and medicinal chemistry.We were driven by our discovery that the dithiasugar analogs of the short β-(1→3)-glucan, laminaritriose…


Natural Product-Inspired Peptide Cyclization Strategies and Their Therapeutic Applications

Peptide cyclization methods are useful in the development of therapeutic peptide leads with improved metabolic stability properties. To develop residue-selective peptide cyclization strategies, we draw inspiration from cyclic and lassoed peptide natural product scaffolds that exhibit diverse biological activities. For example, the reactive phenolic linkages found in both the arylomycin and vancomycin families of antibacterial natural products…


Guest Speaker: Prof. Mark Levin


Asymmetric Anion-Pairing Catalysis


Photoredox Catalysis in Late-Stage Aryl C(sp3 )−H Functionalizations

The high prevalence of aromatics in natural products and potential drug candidates makes them intriguing candidates for continued development of C-H functionalization reactions that proceed with high positional selectivity. Achieving site-selectivity can be a steep challenge as when there is a lack of appropriate directing groups or substitution patterns, more than one product isomer is commonly produced. Therefore, the development of aromatic C…


Pure and Applied Chemistry of Trisubstituted Hydroxylamines: From Reaction Discovery to Drug Design

The presence of a heteroatom-heteroatom bond is a “structural alert” in medicinal chemistry, of which the hydroxylamine N-O bond, with its bond dissociation energy of 55-65 kcal·mol-1 and reputation for inherent mutagenicity and genotoxicity, is a pertinent example.1-3  Due to this broad moratorium, hydroxylamines are overwhelmingly excluded in medicinal chemistry optimization schemes and have thus received little attention from the…


Strained Cyclic Allenes in Stereoselective Reactions and Total Synthesis of Lissodendoric Acid A

Strained Heterocyclic Allene systems are an underexplored building block in chemical synthesis, in spite of being known for more than five decades. Recent advances in azacyclic allenes showed inherent axial chirality that can be transferred to cycloaddition products to obtain highly complex polycyclic systems stereoselectively. With the total synthesis of Lissodendoric acid A is demonstrated that cyclic allenes are a powerful tool for…


“The field of organic chemistry is not exhausted”: Baeyer–Villiger Monooxygenases as a Tunable Biocatalyst

Despite the indispensable role they play in modern society, the pharmaceutical and chemical industries often find themselves contending with a less-than-favorable public image, primarily due to concerns surrounding pollution, accidents, and misinformation. Yet, the advent of “Green Chemistry” offers a glimmer of hope for addressing these challenges by not only minimizing environmental impact but also enhancing the efficiency of production…


The Enabling Role of Substrate Driven Conformational Changes in Enzyme Catalysis


Guest Speaker: Prof. Mingji Dai

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