Kate Kostenkova
Speaker's Institution
Colorado State University
4:00 PM
Virtual Seminar - Zoom
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About the Seminar:

This work will explore photoredox-Ni dual catalyzed sp2-sp3 cross-coupling, Diels-Alder, and hetero Diels-Alder reactions towards their use in synthesizing synthetic cannabinoids. These transformations are critical for medicinal chemistry applications to enable reactions between electron-rich dienes and electron-rich dienophiles and difficult sp3-sp2 cross-coupling reactions.  Additionally, these reactions can be used to synthesize JWH133 and nabilone, synthetic cannabinoids and potential candidates to treat Alzheimer’s.1 An increased interest in cannabinoids for various medicinal applications creates a need for robust synthetic methods. Traditionally, cannabinoids have been synthesized using hetero Diels-Alder reactions which often involve elevated temperatures and pressures.2,3 These methods are often not feasible which creates a need for alternative synthetic routes. Photoredox-catalyzed reactions will provide easier access to reactive radical intermediates, resulting in more high-yielding syntheses and easier derivatization of compounds.4-7 The objective of this proposal is to obtain fundamental knowledge about using photoredox-catalyzed sp2-sp3 cross-coupling, Diels-Alder and hetero Diels-Alder reactions to synthesize biologically relevant molecules. For example, JWH133 and nabilone (Figure 1), which are synthetic cannabinoids of high interest that have been studied for the treatment of Alzheimer’s disease, will be used as a proof of concept to utilize proposed transformations.1 The proposal will determine 1) the substrate scope of photoredox-Ni dual catalyzed sp2-sp3 cross-coupling and Diels-Alder reactions and 2) the choice of the catalyst for photoredox-catalyzed hetero Diels-Alder reactions. Ultimately, this knowledge will be used to provide easily accessible transformations to make other synthetic cannabinoids that are difficult to access via traditional synthetic transformations.

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Meeting ID: 937 1131 3540

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