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Filtering by: Creator Lewis, Norman G. Remove constraint Creator: Lewis, Norman G. Advisor White, James D. Remove constraint Advisor: White, James D.

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  • 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

  • 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:
    obliged to Professor Rich G. Carter, Paul R. Blakemore and Kevin P Gable from the Department of Chemistry

  • 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:
    . I would also like to thank my committee members, Dr. Paul Blakemore, Dr. Rich G. Carter, Dr. Kevin

  • Synthetic transformations of shikimic acid

    Creator:
    White, Edward D., III
    Abstract:
    Four strategies which involve synthetic elaboration of the shikimate nucleus are discussed. Methyl shikimate was differentially protected as the 3,4-0-cyclopentylidene ketal and as the 5- 0- tert- butyldiphenylsilyl ether. The methyl ester was then reduced with diisobutylaluminum hydride and the resulting allylic alcohol was oxidized to aldehyde 47 with pyridinium...
    Resource Type:
    Masters Thesis
    Full Text:
    was reacted in a Lewis acid catalyzed Diels-Alder reaction with 3,5-dimethylfuran to give 77

  • Approaches to the synthesis of trichothecane sesquiterpenes

    Creator:
    Thomas, James Anthony
    Resource Type:
    Dissertation

  • 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:
    50 was 46:54. The use of very strongly acidic media (e. g. trifluoroacetic acid or mineral or Lewis

  • 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:
    ethyl (N-tosylimino)acetate (22) under either thermal or Lewis acid-catalyzed conditions. A mixture of

  • Synthetic studies n bioactive natural products. Part I, An approach towards the nootrophic agent huperzine A. Part II, Synthesis of the tricarbonyl subunit of rapamycin

    Creator:
    Jeffrey, Scott C.
    Resource Type:
    Dissertation
    Full Text:
    Henderers, and Sky High Youth Group A Special Thanks to Heather G. McBride and Dan Henderer

  • 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:
    committee members, Professor Rich G. Carter, Professor Paul R. Blakemore, Professor Kevin P. Gable and

  • 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:
    , Professor Dr. Rich G. Carter, Dr. Miroslav Terinek, Dr. David Ihle, Helmars Smits, Keith Schwartz, David