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  • Studies toward the synthesis of halichlorine and pinnaic acid

    Creator:
    Korf, Eric A.
    Abstract:
    Three approaches toward the core of halichlorine and pinnaic acid are described. The first approach entails a racemic transannular nitrone-olefin [3+2] cycloaddition from nitrone 238. Construction of the nitrone 238 began with aldehyde 241. Another key feature in this route involved a ring-closing metathesis for the formation of a 14-membered...
    Resource Type:
    Dissertation
    Full Text:
    DISSERTATION OF Eric A. Korf for the degree of Doctor of Philosophy in Chemistry presented on July 24

  • A Pyrone Diels–Alder Approach to Substituted Indoles and Carbazoles and the Synthesis of New Ropinirole Analogues

    Creator:
    Points, Gary L., III
    Abstract:
    Aromatic heterocycles are core structural motifs in natural products, pharmaceuticals and biological polymers. Indoles, in particular, represent a significant subclass of aromatic heterocycles, both in terms of sheer numbers, but also in biological and pharmaceutical relevance. As such, new methodologies for the synthesis of indoles represent an important and continually...
    Resource Type:
    Dissertation
    Full Text:
    : A Pyrone Diels–Alder Approach to Substituted Indoles and Carbazoles and the Synthesis of New

  • Part I: Synthesis and evaluation of synosutine as an inhibitor of serotonin, norepinephrine, and dopamine transporters Part II: Asymmetric approach to the tetracyclic core of neomangicol A

    Creator:
    Juniku, Rajan B.
    Abstract:
    Part I: Racemic and asymmetric syntheses of a new substance with prospective antidepressant properties were achieved. In vitro assays with synthetic racemates (±)-25 and (±)-26 suggested that the former is a relatively selective inhibitor of serotonin transporter whereas the latter is a more balanced inhibitor of both serotonin and norepinephrine...
    Resource Type:
    Dissertation
    Full Text:
    Dopamine Transporters Part II: Asymmetric Approach to the Tetracyclic Core of Neomangicol A

  • Atropisomeric 8,8'-biquinolyl derivatives : synthesis, properties and applications

    Creator:
    Milicevic, Selena D.
    Abstract:
    7,7'-Dihydroxy-8,8'-biquinolyl (azaBINOL) was prepared from 7-hydroxyquinoline via N,N-dimethyl O-quinol-7-yl carbamate by directed ortho-metallation followed by FeCl₃-mediated oxidative coupling of the 8-lithioquinoline intermediate. Saponification of the resulting dicarbamate provided crystalline (±)-azaBINOL in 56% overall yield. 6,6'-Bis(dimethylaminocarbonyl)-7,7'-dihydroxy-8,8´-biquinolyl was prepared from the same dicarbamate by a double anionic-Fries rearrangement in 43% yield. 7,7'-Bis(diethylamino-carbonyloxy)-6,6'-diiodo-8,8´-biquinolyl...
    Resource Type:
    Dissertation
    Full Text:
    -8,8´-biquinolyl was prepared from the same dicarbamate by a double anionic-Fries rearrangement in 43

  • Analysis of the mechanism of sulfoxide-lithium exchange and the reactive intermediate in stereospecific reagent-controlled homologation (StReCH)

    Creator:
    Hoyt, Amanda
    Abstract:
    The stereospecific reagent-controlled homologation (StReCH) of boronic esters with enantioenriched carbenoid species generated in situ by the addition of organolithium initiators to stereodefined α-chloroalkyl aryl sulfoxides was previously reported. The reaction of an organolithium with an α-chloroalkyl aryl sulfoxide ostensibly generates an α-chloroalkyllithium via sulfoxide-lithium exchange; however, the true nature...
    Resource Type:
    Masters Thesis
    Full Text:
    chlorosulfoxide-based StReCH is not certain. It may be: an α- chloroalkyllithium, a sulfurane intermediate en

  • Stereocontrolled Synthesis of Allenes by Eliminative Cross-Coupling of Carbenoids

    Creator:
    Cao, Yang
    Abstract:
    The bimolecular reaction of two carbenoid species resulting in the formation of a carbon-carbon double bond (pi-system), referred to herein as carbenoid eliminative cross-coupling (CEXC), involves a series of three fundamental steps: (i) ate-complex formation (transmetalation), (ii) 1,2-metalate rearrangement, and (iii) beta-elimination. All three steps are stereospecific and so the...
    Resource Type:
    Dissertation
    Full Text:
    of a carbon-carbon double bond (pi-system), referred to herein as carbenoid eliminative cross

  • Graphite intercalation compounds containing fluoroanions

    Creator:
    Katinonkul, Watcharee
    Abstract:
    New chemical synthesis strategies have been investigated for the preparation of acceptor-type graphite intercalation compounds (GIC's) with fluoroanions in order to obtain new materials and to develop a better understanding of the synthetic approaches and properties of the products. New GIC's containing borate chelate anion such as bis(oxalato)borate, CxB[OC(O)C(O)O]₂•δF, are...
    Resource Type:
    Dissertation
    Full Text:
    ) Figure Page 5.1 Powder XRD pattern of stage 1 products of (a) CxB[OC(CF3)2C(CF3

  • Stereospecific Synthesis of Stereotriad Motifs and Alkenes Using Enantioenriched sp³-Hybridized Carbenoids

    Creator:
    Xun, Sun
    Abstract:
    Enantioenriched sp³-hybridized carbenoid reagents CR1R2MX (X = nucleofuge, M = electrofuge) of different types were investigated for the synthesis of polysubstituted alkyl chains by iterative stereospecific reagent-controlled homologation (StReCH) and for the stereospecific connective synthesis of alkenes by eliminative cross-coupling. In the first part, putative enantioenriched α-chloroalkyllithiums (CHRLiCl) were employed...
    Resource Type:
    Dissertation
    Full Text:
    proceeds by a pair of fundamental steps both of which are inherently stereospecific: (i) electrophilic

  • Synthesis and catalytic applications of derivatives of 7,7'-dihydroxy-8,8'-biquinolyl (azaBINOL)

    Creator:
    Wang, Chao
    Abstract:
    The synthesis of axially chiral polyfunctional derivatives of 8,8'-biquinolyl was explored and the catalytic action of appropriate derivative types investigated in three separate processes: (1) the silylcyanation of carbonyl groups and imines, (2) alkylation of a glycine Schiff-base via phase transfer-catalysis, and (3) direct amide bond formation from simple amines...
    Resource Type:
    Dissertation
    Full Text:
    processes: (1) the silylcyanation of carbonyl groups and imines, (2) alkylation of a glycine Schiff-base

  • Proteomic approach to the analysis of DNA-binding proteins using mass spectrometry

    Creator:
    Stapels, Martha Degen
    Abstract:
    In proteomic studies, separate experimental protocols have been necessary to identify proteins, determine their function, and predict their three-dimensional structure. In this study, a function-based separation of proteins was conceived to fractionate proteins prior to enzymatic digestion. In the initial demonstration of this technique, a DNA substrate was used to...
    Resource Type:
    Dissertation
    Full Text:
    predict their three-dimensional structure. In this study, a function-based separation of proteins was