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Filtering by: Creator McKinnon, P. F. Remove constraint Creator: McKinnon, P. F. Advisor White, James D. Remove constraint Advisor: White, James D. Resource Type Dissertation Remove constraint Resource Type: Dissertation

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  • The total synthesis of (-)- acorenone B ; Approaches to the synthesis of mycosporin (P 310)

    Creator:
    Ruppert, John Fredrick
    Resource Type:
    Dissertation
    Full Text:
    the synthesis of mycosporin (P 310) AN ABSTRACT OF THE THESIS OF John Fredrick Ruppert for the

  • Synthesis of epothilones and epothilone analogues

    Creator:
    Sundermann, Kurt F.
    Abstract:
    A convergent synthesis of epothilone B that generates all seven of its asymmetric centers in a completely stereoselective fashion has been completed. Key reactions include an anti-Felkin aldol condensation to set the C6 and C7 stereochemistry, a directed α-hydroxylation to install the C15 (S)-hydroxyl substituent, and a Wittig condensation to...
    Resource Type:
    Dissertation
    Full Text:
    AN ABSTRACT OF THE DISSERTATION OF Kurt F. Sundermann for the

  • 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:
    characterization of the new salen ligand and its complexes with various transition and p- block metals. Chapter 3

  • Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

    Creator:
    Li, Yang
    Abstract:
    Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient...
    Resource Type:
    Dissertation
    Full Text:
    . Schell, F. M.; Cook, P. M. J. Org. Chem. 1984, 49, 4067. 30.  Winkler, J. D.; Axten, J. M. J. Am

  • 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:
    /MeCN (1:1), rt, 24h Scheme 12 12 References 1 (a) Searle, P. A.; Molinski, T. F. J. Am

  • 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:
    , Professor Rich G. Carter, Professor Paul R. Blakemore, Professor Kevin P. Gable, Professor Janet Tate and

  • Approaches to the synthesis of polyketides. Vermiculine

    Creator:
    Kirkemo, Curtis Lee
    Abstract:
    An approach to the generation of polyketides was investigated, which involved ozonolysis of 6, 7 cyclopenteno -1> 4, 5, 8 -tetrahydromethoxy- 3-methylnaphthalene (26), to produce what is believed to be polyketide 27. Compound 26 was formed by the following sequence: Die ls -Alder addition of 1, 2 -dim.ethylenecyclopentane and 2...
    Resource Type:
    Dissertation
    Full Text:
    ester was converted to alcohol 113 by the action of isopropenyl ace- tate and p-toluenesulfonic acid

  • 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:
    of 76 and 66 with phthalimidoacetyl chloride respectively. Attempted p-lactam formation by

  • Studies toward the total synthesis of phorboxazole A

    Creator:
    Kuntiyong, Punlop
    Abstract:
    Studies toward the total synthesis of a highly potent cytotoxic marine natural product, phorboxazole A, were conducted and resulted in a route to an advanced intermediate, C4-C32, for this purpose. A key feature of our approach is the stereoselective synthesis of two cis-2,6-disubstituted tetrahydropyrans present in the macrolide portion of...
    Resource Type:
    Dissertation
    Full Text:
    , deprotection of the p-methoxybenzyl ether, and Dess-Martin periodinane oxidation gave aldehyde 25. Wittig

  • The synthesis of trisporic acids

    Creator:
    Prisbylla, Michael Paul
    Abstract:
    A total synthesis of the fungal hormones, trisporic acids A and B, is described, starting from a -methyltetronic acid 34. A Robinson annelation of 34 with ethyl vinyl ketone affords the lactone 33. Treatment of 33 with N-bromosuccinimide gave 97, which was hydrolyzed to the lactol 103. The reaction of...
    Resource Type:
    Dissertation
    Full Text:
    : Redacted for Privacy Professo f Chemistry in charge of major /) Redacted for Privacy Chairman of