Tags: Organic Seminar


Guest Speaker: Prof. Marvin Parasram


New Strategies for Stereoselective Radical Biocatalysis

Radical reactions have enjoyed widespread applications in both small molecule and macromolecule synthesis. However, it remains challenging to control the stereochemistry of radical transformations and to discover novel modes of radical catalysis which are not known in either organic chemistry or biochemistry. Combining synthetic chemistry, enzymology and protein engineering, our group advanced two new biocatalytic strategies for stereoselective…


Recent Total Syntheses of Vinigrol

Vinigrol, a natural product first isolated in 1987, has been studied extensively due to its unique structure and biological properties, including antihypertensive and platelet aggregation-inhibiting effects. Vinigrol has a unprecedented 6-6-8 tricyclic ring system with an axial four-carbon bridge, eight contiguous stereocenters, and a strained bicyclo[5.3.1]undecane ring similar to taxol. A combination of the complex structure and impressive…


α,β-Unsaturated Platinum Carbenes: New Avenues for Diverse Heterocycle Synthesis

The development of catalytic complexity-building transformations is essential to efficient synthetic design.1  The capacity of a single catalyst to induce multiple bond-forming events can facilitate the rapid construction of molecules of interest. Due to the abundance of heterocycles in pharmaceutical agents and natural products, heterocyclizations coupled to additional processes can be advantageous toward the synthesis of medicinally…


Literature Seminar: Margaret Solecki


Recent Applications of Photoexcited Nitroarenes in Organic Synthesis

The photochemical activity of nitroarenes was first reported by Ciamician and Silber in 1901 when the unusual rearrangement of 2-nitrobenzaldehyde to 2-nitrosobenzoic acid was disclosed.1 The cyclization of photoexcited nitroarenes to ortho alkene and alkyne systems was described not long thereafter.2,3 Subsequent work by Ward4 and others5 defined the reactivity of photoexcited nitroarenes as an excitation, analogous to that of carbonyl groups…


Enzymatic Catalyzation of Diazo Compounds for the Formation of Lactones: An Intramolecular C–H Functionalization Strategy

Diazo compounds were first discovered by Peter Griess in 1858.1 The diazo group has been widely used due to its diverse reactivity, including alkylation, carbene generation, nucleophilic addition, homologation, and ring expansion.  These compounds can react with a wide number of transition metal complexes capable of transferring carbenes, including carbene insertion reactions into C–H, Si–H, N–H, O–H, and S–H bonds, sulfur ylide mediated…


Total Synthesis of Gelsemium Alkaloids and Synthesis of Ketohydroperoxides

    The Gelsemium alkaloids were first isolated from Gelsemium elegans and sempervirens in the 1870s. Despite their acute toxicity, they were documented for their potent analgesic properties and were first used in traditional Asian medicine. Our group achieved the first total synthesis of gelsenicine in 2016 using an Au(I)-catalyzed cycloisomerization/Cope rearrangement to forge the oxabicyclo[3.2.2]nonane skeletal…


Synthesis of Erythropoietin

Since approval by the FDA in 1989, erythropoietin (EPO) has been used extensively for the treatment of anemia – especially in those with chronic kidney disease, undergoing chemotherapy, or have acquired immune deficiency syndrome (AIDS).1 EPO is a highly glycosylated glycoprotein containing three N-linked and one O-linked glycosylation sites. These glycans constitute 40% of the weight of the glycoprotein and are important for activity.2 It has…


Synthesis and Application of Functional Nanoparticles for Precision Drug Delivery

Nanoparticles (NPs) are particles of approximately 1-100 nm in size and have properties not found in bulk samples of the same material. Different materials, such as polymers, metal oxides, silica, noble metals, and carbon, can be used to create nanoparticles, which can then carry a variety of bioactive substances for use in biomedical applications, such as proteins, nucleic acids, small molecules for chemotherapy, and diagnostics. Owing to their…
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