Tags: Organic Seminar


Comparative Study of Photochemically Generated Conjugated Ortho- and Para-Quinone Methide Reactivity

Isomeric ortho- and para-quinone methides, while possessing similar electronic structures, show very different properties. o-Quinone methides (oQM) are more reactive towards nucleophiles and undergo very fast and efficient inverse electron-demand-Diels-Alder (IEDDA) reaction with electron-rich alkenes. p-Quinone methide, while also acting as Michael acceptors, is not reactive in IEDDA. The photochemical generation of o-naphthoquinone methide (o…


Total Syntheses of Pepluanols A and B

Euphorbia is a large and diverse genus of flowering plants in the spurge family, comprising more than 2,000 species.1,2 Many of them have long been used in herbal folk medicine. In 2016 and 2018, Qiu and co-workers isolated five diterpenoids, pepluacetal and pepluanols A–D, from Euphorbia peplus.3,4 All five compounds show effective inhibitory activity on the KV1.3 voltage-gated potassium channel. Thus, they are potential candidates for the…


Design, Development and Planned Proof of Concept for a Gate Functionalized Drug Delivery Metal Organic Framework (MOF)

It might be an understatement in saying the interest in Metal Organic Frameworks (MOFs) and their vast array of topologies, constitutions and applications have incurred great interest over the past two decades. Many areas of chemical research have been impacted in the potential that MOFs bring to the table. These include gas storage and separations, chemical catalysis, endeavors in the removal of harmful and toxic environmental chemicals,…


The Total Synthesis of Daphniphyllum Alkaloids

Daphniphyllum alkaloids have a rich history dating back to the isolation of Daphniphyllum macropodum Miquel in 1909 by Yagi.1 Pioneering work in the 1960s by Hirata and colleagues resulted in the isolation of daphniphylline and yuzurimine alkaloids, and subsequently, a total of over 330 Daphniphyllum alkaloids have been reported from the Daphniphyllum genus.2-5 In view of their intriguing biological activities including anti-cancer and…


Advances in Chromium(III) Photocatalysis: Catalyst Design and Reaction Development

Over the past few decades, photoredox catalysis has emerged as a powerful tool for new bond formation. Acting as an oxidant or a reductant, an excited-state metal complex can generate reactive radical intermediates via a single-electron transfer process. The most commonly used transition-metal photocatalysts are ruthenium or iridium complexes. Our group has utilized chromium(III) complexes in a variety of different photoredox transformations.…


The Valorization of Lignin and its Roles in the Landscape of Bio-Based Materials

Lignin is the world’s second most abundant biopolymer and the world’s largest source of biobased aromatics (1). Occurring as an adhesive which binds together the cellulose fibers in the cell walls of woody plants, lignin has been largely cast aside as a waste byproduct of pulping procedures. Since the main industrial pulping procedures focus on the production of paper, the fate of lignin usually involves combustion to produce heat (2). This…


Recent Advances in Electrocatalytic C-H Activation

Electrolysis in synthetic organic chemistry has a rich history dating back to the 19th century. Many advances have been done with the use of electrolysis in the past, e.g. Kolbe’s decarboxylative dimerization, 1 Tafel’s electrolytic rearrangement, 2 Simmons’s C-H fluorination.3 Since then the popularity of the electrolysis in synthetic organic chemistry has drastically decreased. In the past decade transition metal-catalyzed C-H…


AaronJr: Automates Any Reaction or Optimization, Normally Just Right

Despite the ever-increasing availability and applicability of computational methods to questions of chemical significance, many chemists from purely experimental backgrounds find it difficult to begin integrating these methods into their research. To reduce this barrier of entry and catalyze non-computational chemists’ ability to take advantage of the insights computational studies can provide, we have developed a suite of tools, collectively…


Synthesis of Chemical Tools for the Study of Protein O-Mannosylation

Glycosylation of certain proteins by oxygen-linked mannose (O-mannose) is known as O-mannosylation, and this process is essential for growth and development in animals.1-4 Defective O-mannosylation of α-dystroglycan, the most well studied O-mannosylated mammalian protein, leads to congenital muscular dystrophies and neurological defects.4-6 Mannose is linked to proteins through the serine or threonine side chain oxygen. Glycosyl transferase…


Road to Phorbol

Phorbol, a Tigliane natural product first isolated in 1934 by Dr.Flaschenträger and Dr. Wolffersdorff, drove 17 research groups to develop the synthesis of it for over 30 years and report over 40 synthesis papers because of their potent biological activities to promote the tumor by activation of the protein kinase C and the anticancer activity.  The structure of the phorbol, first determined by Dr. Heck in 1967, was a congested tetracyclic…
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