Tags: Organic Seminar


Design of a Novel Photocleavable Metal-Organic Framework

Metal-Organic Frameworks (MOFs) since their discovery have been used in a variety of applications, including, but not limited to gas adsorption and storage, food packaging, biofilms and drug delivery. This is attributed to the vast array of options for its component parts (the metal nodes and the organic linkers) and its high surface area and high porosity. Recently, there has been a surge of MOFs in the drug delivery realm, especially in the…


From “Intentional Avoidance” to “Resurgence” - Development of Covalent Inhibitors in Drug Discovery

The use of covalent inhibitors in the field of drug discovery has attracted considerable attention in the 2000s. But largely owing to safety concerns, they are rarely considered when initiating a target-directed drug discovery project. Thanks to modern drug discovery approaches, the development of covalent inhibitors has been flourishing in the past decade. Covalent inhibitors are small molecules with a warhead that form a covalent bond with…


Developing a Methodology for Probing Student Comprehension of Organic Chemistry Using Eye Tracking Technology

Eye tracking technology has been used to study comprehension through visual processing in a variety of fields, but has seen a significantly increased use in chemistry in the past decade. Organic chemistry in particular uses unique visual representations to convey information, which could make information obtained by eye tracking particularly relevant for understanding student comprehension of the material being discussed. While this has been…


Palladium Catalyzed C−H Lactonization of Aliphatic Acids

C−H activation has gained extensive attention as a powerful tool in synthetic organic chemistry. The carboxylate moiety is believed as a promising candidate, however, the C−H activation of carboxylic acid is highly challenging because of its weak directing ability. In recent years, the development of novel palladium catalysis strategies allows the utility of aliphatic acid in C(sp3)−H functionalization, and notably lactonization…


Synthesis of N,N,O-Trisubstituted Hydroxylamines (Hydroxalogs) and Other Projects

There has been a continuous need to enrich small molecule libraries with underrepresented functional groups to increase the chance of finding potential drug candidates. N,N,O-trisubstituted hydroxylamine is such a functional group that has been underrepresented in drug discovery due to concerns about its stability and mutagenicity. However, the trisubstituted hydroxylamine functionality has multiple features that make it suitable as a drug…


Confronting Pathogens with a Combination of Synthetic and Analytical Chemistry

The Manetsch laboratory focuses on synthetic chemistry and the development of LC/MS-guided medicinal chemistry approaches for the development of anti-infective agents. The first half of the seminar focuses on the streptothricin natural products class, while kinetic Target-Guided Synthesis (kTGS) is the topic of the second half of the seminar. Streptothricins are highly active against gram-positive and gram-negative ESKAPE pathogens. Common…


Total Synthesis of the Herqulines

The herquline family of natural products were originally isolated from penicillium herquei in 1979 by the Ōmura group (see figure below). These strained macrocyclic alkaloids all contain multiple stereocenters, and an unsymmetrically substituted piperazine. Herqulines B and C feature two β,γ-unsaturated cyclohexenones, while herquline A bears an additional pyrrolidine. In the intervening years since their isolation, numerous failed synthetic…


Metal–Hydrogen Atom Transfer (MHAT)-Initiated Intramolecular Giese Reactions in Total Synthesis

The use of metal–hydrogen atom transfer (MHAT) for olefin hydrofunctionalization has received great attention over the last 20 years, primarily due to its enhanced chemoselectivity and regioselectivity.[1] The Giese reaction, or the addition of a carbon-centered radical into an electron-deficient alkene, is well-known and has been commonly employed for C–C bond formation over the last 40 years.[2] More recently, the Baran group coupled these two…


Cycloadditions Enabled by Chromium(III) Photoredox Catalysis

Photoredox catalysis has emerged as an integral fraction of modern organic methodology.[1] Since the early 2000’s there has been a renewed interest in photochemistry, with photoredox catalysis utilizing visible light becoming a rapidly expanding field. Various transition-metal complexes have been developed and proven efficient photocatalysts; however, the two most commonly employed metals in these systems are the incredibly expensive, rare-earth…


Guest Speaker: Prof. Kami Hull

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