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Filtering by: Creator Feely, R. A. Remove constraint Creator: Feely, R. A. Advisor White, James D. Remove constraint Advisor: White, James D. Resource Type Dissertation Remove constraint Resource Type: Dissertation

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  • 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:
    of (R)- and (S)- MTPA esters of 166…….. 1H NMR Spectra of Synthetic (a) and Natural (b

  • Studies towards the total synthesis of (-)-kendomycin

    Creator:
    Smits, Helmars
    Abstract:
    Studies towards the total synthesis of (−)-kendomycin (1), a bacterial metabolite with a unique molecular architecture and pronounced biological activity, are described. These studies resulted in the synthesis of advanced intermediate 208, containing all of the carbon atoms of 1. A Dötz annulation between alkyne 122 and novel chromium carbenoid...
    Resource Type:
    Dissertation
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    :_____________________________________________________ James D. White Studies towards the total synthesis of (−)-kendomycin (1), a bacterial

  • 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:
    . A.; Werkman, R. F.; Koch, K. L. Gastrointest. Endosc. 2003, 58, 30. 3. Bren, L. Frances Oldham

  • 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
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    .; Nicholson, A. A.; Tchir, M. F. Can. J. Chem. 1969, 47, 711. 8. (a) Kearns, D. R.; Marsh, G.; Schaffner, K

  • Synthesis of marine natural products. part I, Cryptophycins-1, -3, -4, -24, and -29, part II, Polycavernoside A

    Creator:
    Robarge, Lonnie A.
    Resource Type:
    Dissertation
    Full Text:
    1 -4, and (C) the (R)-O-methyltyrosinyl residue of 2, 4, and 5 which bears a m-chloro substituent

  • 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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    .; Baran, P.; Raptis, R. G. Org. Lett. 2003, 5, 2551. 2. Roethle, P. A.; Trauner, D. Nat. Prod. Rep. 2008

  • 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
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    steps 12: R = Bn 13: R = H H2, Pd/C, EtOH 25 ºC 100% TPAP, NMO, 4 A MS DCM, 25 ºC O O O PivO O P

  • 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
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    product of phorboxazole A with synthetic (S)- and (R) - dimethyl methoxysuccinate using chiral GCMS. The

  • Asymmetric synthesis of cyclopropanes via a "zipper reaction"

    Creator:
    Lincoln, Christopher M.
    Abstract:
    The rearrangement of a homoallyl cation to a cyclopropylcarbinyl cation is thought to play a role in the biogenesis of a variety of cyclopropane-containing natural products,¹ a hypothesis which has previously led to the design of successful biomimetic syntheses of several natural products.² The strategy underlying this approach to cyclopropane...
    Resource Type:
    Dissertation
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    Synthesis of Cyclopropanes via a "Zipper Reaction" Abstract approved: James D. White The rearrangement of

  • Approaches toward the asymmetric synthesis of pillaromycin A

    Creator:
    Nolen, Ernest G.
    Resource Type:
    Dissertation
    Full Text:
    active against a broad range of solid tumors in man. As a class R1=H; R 2 =Me, daunomycinone R1 =0H