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Filtering by: Creator Jackson, Alexis M. Remove constraint Creator: Jackson, Alexis M. Committee Member Gable, Kevin Remove constraint Committee Member: Gable, Kevin Degree Field Chemistry Remove constraint Degree Field: Chemistry

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  • Stereoselective synthesis & application of enantioenriched main group α-haloalkyl organometal reagents

    Creator:
    Emerson, Christopher R.
    Abstract:
    Sulfoxide-ligand exchange (SLE) and asymmetric halogen-metal exchange (AHME) processes were separately examined for the enantioselective synthesis of functionalized alpha-haloalkylmetal (carbenoid) reagents. Carbenoids derived from SLE were used to effect stereospecific reagent-controlled homologation (StReCH) of boronic esters and those generated via AHME were engaged in Darzens-type chemistry with aldehydes. Abstract for...
    Resource Type:
    Dissertation
    Full Text:
    Jackson-Ellman-Bolm catalytic enantioselective sulfoxidation [cat. VO(acac)2, tert-leucinol derived

  • Studies toward the total synthesis of sanglifehrin A

    Creator:
    Suttisintong, Khomson
    Abstract:
    Studies toward synthesis of subunits of sanglifehrin A, an immunosuppressant featuring a highly substituted [5,5]-spirolactam moiety as well as a 22-membered macrocycle are described. The macrolactone contains a peptidic backbone characterized by an unusual [beta]-substituted (S)-piperazic acid and (S)-m-hydroxyphenylalanine units. These studies resulted in the synthesis of advanced intermediate 358...
    Resource Type:
    Dissertation
    Full Text:
    a peptidic backbone characterized by an unusual β−substituted (S)-piperazic acid and (S)-m

  • 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:
    = nucleofuge, M = electrofuge) of different types were investigated for the synthesis of polysubstituted

  • 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:
    Preparative chromatographic separations were performed on silica gel 60 (35-75 μm) and reactions followed by

  • 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:
    favorite natural product, to my wife, Alicia M. Juniku, and to my family residing both in Europe and

  • Development and Application of Mass Spectrometry-driven Methods for the Detection and Characterization of Biomolecular Signatures of Diseases

    Creator:
    Zandkarimi, Fereshteh
    Abstract:
    State-of-the-art, high-resolution mass spectrometry techniques for acquisition of metabolomic and lipidomic data coupled with advanced computational methods provide new opportunities for interpreting large and complex datasets and comprehending the underlying biological processes of diseases. Both metabolomics and lipidomics strive to obtain comprehensive analyses of small molecules, i.e., metabolites and lipids,...
    Resource Type:
    Dissertation
    Full Text:
    panel), and 3D (m/z vs. drift time vs. counts; right panel) driftograms from UPLC-TWIMS-MS (ESI

  • 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:
    performance in the silylcyanation of benzaldehyde, as noted in the text. Mr. Darrin M. Flanigan conducted

  • 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:
    spectra corresponding to crosslinked peptides from CspC: (A) precursor with m/z 1,822.7; (B) precursor

  • 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:
    symmetric cleavage) and the ion at m/z 255 was identified with the unusual ion 33, not found in other

  • 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:
    stereocenter of carbenoid (55) remains the same, the another stereocenter of R2 R1 M’ X’ R3 R4M X M