Tags: Organic Seminar


Light-Induced Nucleophilic Substitution by Photo-activation of a Leaving Group

Nucleophilic substitution reactions are at the heart of synthetic organic chemistry. While conventional strategies for conducting nucleophilic substitution reactions have been heavily studied, we hereby report the development of the novel photochemical approach to the induction of nucleophilic substitution reactions. This strategy employs a light-activated leaving group based on the 9-aryl-9-fluorene system. 9- fluorenol undergoes efficient…


Total Synthesis of Dithiodiketopiperazine Natural Products

Dithiodiketopiperazines or “DKP’s” is common motif that appears in various natural products. These natural products have been shown to display anti-viral or anti-tumor properties. Within the past two decades, an increasing number of natural products have been isolated containing a DKP core. Although synthetic strategy towards this core has been around since the 1960’s, there is still much innovation withing the area of DKP natural product total…


Antibody-Drug Conjugates: Recent Advances in Site-Specific Conjugation Offers Payload Diversity

Antibody-drug conjugate (ADC) development has seen recent improvement through employment of targeted conjugate synthesis strategies. Methods that optimize delivery of antibodies, linkers, and conjugated drug compounds have emerged. Through these methods, higher drug conjugation density, increased linker stability, and lower unconjugated antibody concentrations can be achieved. Dual conjugation, a process by which two different conjugated drugs…


Guest Speaker: Prof. Andrew Lawrence

Prof. Lawrence describes his research as “...primarily focused on the total synthesis of natural products, exploring new strategies and concepts in chemical synthesis, and developing new synthetic methodology.”


Looking Back and Building Forward: Natural Products Biosynthesis

Natural products are organic secondary metabolites produced by all forms of life. In their native environment, natural products mediate intra- and interspecies communication. Bioinhibitory activities of natural products make them medicinally attractive– majority of clinically used drugs and pharmaceuticals are or are derived from natural products. The Agarwal laboratory seeks to understand how gene encoded enzymes construct natural product…


Pfizer Medicinal Chemistry Seminar

As part of the the Spring 2022 Organic Seminar series, on January 27th from 11:10 am we will host a virtual seminar by three representatives from Pfizer’s medicinal chemistry team: Medicinal Chemistry at Pfizer – Dr. Sheneika Jackson Sheneika Jackson completed her Ph.D. at the University of Georgia in May 2021. Under the guidance of Dr. Eric Ferreira, she worked on the development of molecular scaffolds for C-H…


New Tools for Making Computational Quantum Chemistry Simpler

Computational quantum chemistry can be used to gain insight into reactivity and simulate properties or spectra. However, conducting computational studies often requires using command line interfaces, which have a steep learning curve. A simpler alternative to command line interfaces is graphical user interfaces. Existing graphical interfaces are often insufficient to handle every task that one encounters during a computational study: building…


Advancing Photo-Click Chemistry towards Macrocyclization and Sequence-defined Oligomers

Nature uses sequence-defined (having a precise sequence of units) monodisperse (same molecular weight) polymers for the data storage and transfer (DNA, RNA), for the control of properties and structure (proteins), for the efficient catalysis of various reactions (enzymes), and many more. However, these bio-macromolecules have limited stability and lack chemical and structural diversity. Current methods for the preparation of sequence-defined…


Mono-cyclopropenone Caged Dibenzocyclooctyne Triazole Derivatives: Fast-reacting, Water Soluble SPAAC Reagents

Strain-promoted azide-alkyne cycloaddition (SPAAC) has emerged as a popular click chemistry technique1. Over just the past few decades, a plethora of cycloalkyne SPAAC reagents have been developed for use as biorthogonal probes in cell and protein studies2-4, peptide stapling reagents5, and crosslinkers in polymers6. Most of these cycloalkyne reagents suffer from issues that hinder their utility; these being low aqueous solubility and slow…


Stereoselective Synthesis and Applications of Sulfonylcyclopropanols as Modular Cyclopropanone and Homoenolate Equivalents

Cyclopropanone derivatives have long been regarded as unusable and elusive synthetic intermediates, mainly owing to their prominent ring strain and kinetic instability. In this work, we report the enantioselective synthesis of sulfonylcyclopropanols, shown to be modular and versatile synthetic equivalents of the corresponding cyclopropanone derivatives. These reagents were found to smoothly react in a variety of reaction manifolds, including…
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