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    Development of New Anionic Cascades and Analysis of US FDA Drug Architectures

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    Author
    Delost, Michael D.
    Issue Date
    2021
    Keywords
    Analysis of drug architectures
    anionic-amino Cope rearrangement
    asymmetric synthesis
    Darzens reactions
    Oxygen and Nitrogen heterocycles
    trifluoromethylthiolation
    Advisor
    Njardarson, Jon T.
    
    Metadata
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    Publisher
    The University of Arizona.
    Rights
    Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction, presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
    Embargo
    Release after 01/01/2022
    Abstract
    This dissertation is divided into five chapters, encompassing innovative synthetic contributions in the area of Darzens annulations, anionic-amino-Cope cascades, structural analysis of FDA-approved pharmaceuticals as well as book chapter contributions in highlighting synthetic contributions in oxirane and aziridine chemistry. Chapter 1 presents two-book chapter contributions made which highlight synthetic contributions made with oxiranes and aziridines. Part 1: focuses on synthetic contributions made with oxiranes (epoxides) from 2008-2018. Part II focuses on homologation approaches to access oxiranes and aziridines from carbonyl and imines. Chapter II presents two-published perspectives, published in the Journal of Medical Chemistry. Part I analyzes oxygen-heterocycles seen in FDA-approved pharmaceuticals. Part II analyzes the structural diversity in FDA-approved combination drugs. Chapter III: presents novel contributions made in the arena of anionic-amino-Cope rearrangements (Part I) and applications (Part II). Chapter IV presents novel contributions made with vinylogous (Aza)-Darzens annulations. Part I discusses an asymmetric-vinylogous Aza-Darzens protocol with a bromo-butenolide nucleophile. Part II describes phenyl sulfone-containing vinylogous (Aza)-Darzens routes. Chapter V describe mild protocols to obtain trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes.
    Type
    text
    Electronic Dissertation
    Degree Name
    Ph.D.
    Degree Level
    doctoral
    Degree Program
    Graduate College
    Pharmaceutical Sciences
    Degree Grantor
    University of Arizona
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