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Filtering by: Creator Baldwin, Carole C. Remove constraint Creator: Baldwin, Carole C. Contributor advisor sim White, James D. Remove constraint Contributor advisor sim: White, James D.

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  • Cis-2,5-diaminobicyclo[2.2.2]octane : a novel C₂-symmetric scaffold for asymmetric catalysis

    Creator:
    Shaw, Subrata
    Abstract:
    This thesis describes the development of a new enantioselective synthetic method employing chiral cis-2,5-diaminobicyclo[2.2.2]octane-based organometallic catalysts. The significance of this new method to organic synthesis is illustrated with preparation of enantioenriched products that are transformed to important pharmaceutical agents. Chapter 1 provides a brief historical overview of asymmetric catalysis, especially...
    Resource Type:
    Dissertation
    Full Text:
    structures for DIANANE (26; A (side view)) and cis-2,5-diaminobicyclo[2.2.2]octane (34; B (side view) and C

  • Approaches to the total synthesis of verrucarol

    Creator:
    Hill, David E. (David Edwin) 1954-
    Abstract:
    Verrucarol is the sesquiterpene portion of a number of macrocyclic di- and triesters of potential medicinal importance. In this study, a novel approach to the synthesis of this fungal metabolite is presented. An A-B-C route was investigated in which C-3 and C-4 of the C-ring were emplaced using a [2+2]...
    Resource Type:
    Dissertation
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    fungal metabolite is presented. An A-B-C route was investigated in which C-3 and C-4 of the C-ring were

  • Studies on the synthesis of the "northern" and "southern" segments of boromycin and aplasmomycin

    Creator:
    Kang, Myung Chol
    Abstract:
    The stereocontrolled synthesis of the southern lactone 17 of boromycin and of the northern segments of both boromycin and aplasmomycin are described. The syntheses begin with enantioselective epoxidation of 3-buten-2-ol (42) to provide the optically active 2(S),3(R) epoxy alcohol 43. The absolute configuration was confirmed by preparing 43 from (-)-2,3-dihydroxybutyric...
    Resource Type:
    Dissertation
    Full Text:
    was prepared from 124 for the purpose of adding C(1) and C(2) to aplasmomycin. Studies on the

  • The synthesis of nonactic acid

    Creator:
    Arco, Manuel Jose
    Abstract:
    Alkylation of propylene oxide with 2-lithiofuran gave alcohol I, which was smoothly converted to acetylfuran II. hydrogenation of II over rhodium on charcoal followed by Jones' oxidation afforded ketone III. Further transformation into IV was accomplished via a Wittig reaction followed by saponification with methanolic sodium hydroxide. Hydroboration of the...
    Resource Type:
    Dissertation
    Full Text:
    followed by an inversion of configuration at C-8. Methanolysis of VII afforded methyl nonactate VIII

  • Studies toward the total synthesis of (+)-providencin

    Creator:
    Jana, Somnath
    Abstract:
    Studies toward the total synthesis of (+)-providencin (1), a highly oxygenated cembranoid dipterpene with a unique bicyclo[12.2.0]hexadecane skeleton and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediates 320 and 332 which contain all of the carbon atoms of 1. In a first generation approach...
    Resource Type:
    Dissertation
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    to couple the two major fragments, 228 and 288, using palladium-catalyzed C-H activation of the

  • Approaches to the synthesis of penicillin

    Creator:
    Furuta, Takuya
    Abstract:
    Several approaches to the synthesis of penicillin from 2-iminothioazolidine 50, from 2-thiothiazolidine 66 and by photocyclization of 77 and 78 were investigated. 2-Iminothiazolidine 50 was prepared from dibromoester 45 by the action of benzylamine followed by treatment of aziridine 46 with potassium or ammonium thiocyanate. Attempted introduction of a two-carbon...
    Resource Type:
    Dissertation
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    . RI-IN RI-IN R -CO( CH 2 ) 3 CH COOH NH 2 2 C 00H CH OA c 2 Two major problems arose after

  • Part I : synthesis of azetidin-2-ones from pyrazolidin-3-ones ; Part II : synthesis of a subunit of the immunosuppressant FK-506

    Creator:
    Toske, Steven Gerald
    Resource Type:
    Dissertation
    Full Text:
    Carole A. Toske She gave me love and courage Acknowledgements I would like to thank Professor James

  • Synthetic studies of nonadrides

    Creator:
    Drapela, Nicholas Ernest
    Abstract:
    An asymmetric approach to the synthesis of byssochlamic acid (1) is described. Regioisomeric enzymatic differentiation is described in the selective hydrolysis of dimethyl ester 30 by porcine liver esterase. Chiral dimethyl ester 42 was prepared by desymmetrization of cyclopentene 34 using porcine liver esterase. A key intramolecular [2+2]cycloaddition-cycloreversion photometathesis of...
    Resource Type:
    Dissertation
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    which the maximum temperature attained exceeds 90°C. After several weeks of incubation of the fungus on

  • Total synthesis of indole alkaloids: pt. 1. Asymmetric synthesis of (-)-ibogamine. pt. 2. An approach toward the synthesis of koumine

    Creator:
    Choi, Younggi
    Abstract:
    PART I. The preparation of (-)-ibogamine (1) in fourteen steps from benzoquinone and in 10% overall yield is a powerful illustration of the value of the asymmetric Diels-Alder reaction as a starting point in a multistep synthesis. All four cycloadducts, 70, 77, 84 and 96, obtained with the (S)-BINOL-TiCl₂ complex...
    Resource Type:
    Dissertation
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    (Continued) Table Page C.2 Atomic coordinates (x 104) and equivalent isotropic displacement parameters

  • Synthesis of metabolites from the ascomycetes : I. The synthesis and absolute configuration of leptosphaerin : II. Approaches to the synthesis of byssochlamic acid

    Creator:
    Pallenberg, Alexander J.
    Abstract:
    Part I. The total synthesis of (+)-leptosphaerin (2), a metabolite of the marine Ascomycete Leptosphaeria Oraemaris (Linder) was achieved, unambiguously establishing both the relative and absolute stereochemistry of this natural product. This synthesis also resolved the long-standing question of which of the isomeric structures 1 or 2 correctly represents the...
    Resource Type:
    Dissertation
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    Configuration of Leptosphaerin la I-A. Introduction la I-B. Discussion 4 I-C. Experimental 17 I-D. References