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Filtering by: Creator McAuliffe, Scott C. Remove constraint Creator: McAuliffe, Scott C. Advisor White, James D. Remove constraint Advisor: White, James D. License All rights reserved Remove constraint License: All rights reserved

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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

  • 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:
    to couple the two major fragments, 228 and 288, using palladium-catalyzed C-H activation of the

  • 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:
    cyclization that provided tetracyclic ketone 5.86 containing rings A, B, C and D of vindorosine. A

  • Synthesis of furanoeremophilane sesquiterpenoids

    Creator:
    Shanmugham, Meenakshi Sundaram
    Abstract:
    Two approaches to the tricyclic core of the furanoeremophilane sesquiterpenoids are described. The first approach entails a projected Diels-Alder/retro Diels-Alder reaction of an acetylenic oxazole 64. Construction of the pivotal aldehyde 67 commenced from ketone 68. The acetyenic moiety was then introduced via a Felkin-Ahn addition of lithiopropyne to aldehyde...
    Resource Type:
    Dissertation
    Full Text:
    , Nick Drapela, Uwe Grether, Roger Hanselmann, Josh Hansen, Bryan Hauser, David IhIe, Scott Kemp, Linda

  • 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:
    , Scott J. Kemp, Linda E. Keown, Jungchul Kim, Sung-kee Kim, Eric A. Korf, Christian L. Kranman, Punlop

  • 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:
    Hansen, Carla Hassler, Bryan Hauser, Eric Hong, Peter Hrnciar, Scott Kemp, Linda Keown, Jungchul Kim