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Filtering by: Creator Barry%2C Zachary T. Remove constraint Creator: Barry%2C Zachary T. Advisor White, James D. Remove constraint Advisor: White, James D.

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  • Chiral synthesis of monic acid C

    Creator:
    Theramongkol, Parinya
    Abstract:
    Bromoalkoxylation of dihydropyran with bromine and 1-borneol, followed by dehydrobromination and epoxidation, afforded trans-2-1- bornyloxy-3,4-epoxytetrahydropyran as a major product. This was treated with sodium phenylselenide to give a 1:1 mixture of (2R,3R,4R)- 2-1-bornyloxy-3-hydroxy-4-phenylselenotetrahydropyran and its (2S,3S, 4S) diastereomer. Elimination of the selenoxide, derived from oxidation of the former with hydrogen...
    Resource Type:
    Dissertation
    Full Text:
    mixture of (2S,3S,4R,5S)-2-(3-methyl)-(E)-carbo-t- butoxypropeny1)-3,4-cyclohexylidenedioxy-2H-pyran-5

  • Synthetic studies on the macrolide antibiotic rutamycin B

    Creator:
    Wang, Shan
    Resource Type:
    Dissertation
    Full Text:
    .19 The alternative approach to synthesis of rutamycin 0 0 -O.+ ..,... H''e OBz CO2H 4-t

  • 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
    Full Text:
    ) Marrero, J.; Rodriguez, A. D.; Baran, P.; Raptis, R. G.; Sanchez, J. A.; Ortego-Barria, E.; Capson, T. L

  • 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:
    recognized by the 2001 Nobel Prize in Chemistry awarded to William S. Knowles, Ryoji Noyori, and K. Barry

  • 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
    Full Text:
    % 0 Ph T 0 LIi jJ MeO L.CH0 NaBH I 93% Pd(PPh3)4 45% H (+)-Ibogamine (1) Scheme 9. Trost's

  • Part I. The total synthesis of (±)-cinnamodial and related drimane sesquiterpenes; Part II. Photochemical activation of the carboxyl group via N-Acyl-2-thionothiazolidines

    Creator:
    Burton, Lester Percy Joseph
    Resource Type:
    Dissertation
    Full Text:
    stereoselectivity of the hydroboration, 61 was converted to both (t)-isodrimenin (67) and (±)-fragrolide (72) in 3

  • Total synthesis of phorboxazole A

    Creator:
    Lee, Tae Hee
    Abstract:
    The total synthesis of a highly potent cytotoxic marine natural product, phorboxazole A, is described. Both a palladium(II)-mediated and a palladium(II)-catalyzed intramolecular alkoxycarbonylation were used as key steps for the preparation of the two cis-2,6-disubstituted tetrahydropyran rings (C22-C26 and C11-C15) of phorboxazole A. The synthesis used a convergent approach involving...
    Resource Type:
    Dissertation
    Full Text:
    % 30 min, reflux 75% 3 4 6 t-BuOK HCO2Me AcOH 5 Scheme 1 Methyl acetimidate 3 was

  • Approaches toward the asymmetric synthesis of pillaromycin A

    Creator:
    Nolen, Ernest G.
    Resource Type:
    Dissertation
    Full Text:
    )-7-acryloxy-8-acetoxy-2-t-butyldimethyl- siloxy-3,5-nonadiene (59). Three Diels-Alder products were

  • 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
    Full Text:
    COOH 3 8 C1CH2C0C1 NaOH t- BuOOCH NaOt -Bu H H C,)----d liN0 t-BuO0C 1.:C00H H PhOCH 2 COHN

  • Total synthesis of (-)-7-epicylindrospermopsin

    Creator:
    Hansen, Joshua D.
    Abstract:
    The first asymmetric synthesis of (-)-7-epicylindrospermopsin via intramolecular nitrone cycloaddition is described. The synthesis utilized a convergent approach to prepare the cycloaddition precursor 176, which was assembled by condensation of hydroxylamine 175 with aldehyde 145. Hydroxylamine 175 was synthesized from ethylene glycol (166) in seven steps. Aldehyde 145 was completed...
    Resource Type:
    Dissertation
    Full Text:
    106 107 0 OMe97% t 1. (CH3)2C(OMeb TSOH (58 %) 2. HCI (aq) (70 %) 3. a) p-N02C6H4COOH, DEAD