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Filtering by: Contributor Anderson, Kim A. Remove constraint Contributor: Anderson, Kim A. Academic Affiliation Chemistry Remove constraint Academic Affiliation: Chemistry Committee Member Blakemore, Paul R. Remove constraint Committee Member: Blakemore, Paul R.

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  • Studies toward the synthesis of halichlorine and pinnaic acid

    Creator:
    Korf, Eric A.
    Abstract:
    Three approaches toward the core of halichlorine and pinnaic acid are described. The first approach entails a racemic transannular nitrone-olefin [3+2] cycloaddition from nitrone 238. Construction of the nitrone 238 began with aldehyde 241. Another key feature in this route involved a ring-closing metathesis for the formation of a 14-membered...
    Resource Type:
    Dissertation
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    DISSERTATION OF Eric A. Korf for the degree of Doctor of Philosophy in Chemistry presented on July 24

  • 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:
    SYNTHESIS OF C1-C32 MACROLACTONE OF PHORBOXAZOLE A AN

  • A Diels-Alder approach to biaryl synthesis

    Creator:
    Ashburn, Bradley O.
    Abstract:
    An expedient approach to the synthesis of a wide range of highly programmable biaryl templates has been accomplished. Utilizing the Diels-Alder [4+2] cycloaddition, a wide range of tri- and tetra-ortho-substituted biaryls have been synthesized in only three to four steps from commercially available materials. We have successfully synthesized entire classes...
    Resource Type:
    Dissertation
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    . Weinreb, S. M.; Basha, F. Z.; Hibino, S.; Khatri, N. A.; Kim, D. Pye, W. E.; Wu, T.-T. J. Am. Chem

  • Part I: Synthetic studies toward the southern portion of Azaspiracid-1; Part II: Total synthesis of amphidinolide B₁ and the proposed structure of amphidinolide B₂

    Creator:
    Lu, Liang
    Abstract:
    The structural architecture present in marine toxin azaspiracid - 20 stereocenters, 9 rings, 3 separated spirocenters - has attracted considerable synthetic attention. Our efforts toward the synthesis of azaspiracid have led to the completion of both C₁-C₂₆ northern and C₂₇-C₄₀ southern halves. Herein, the synthesis of southern FGHI ring system...
    Resource Type:
    Dissertation
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    ketalization to furnish FG rings, and a Yb(OTf)3-mediated spiroaminal formation to generate I ring. 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
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    Intramolecular Photocycloaddition-retro-Mannich Fragmentation as a Route to Indole and Oxindole Abstract

  • Part I: Total synthesis of marine macrolide amphidinolide F and synthetic studies toward amphidinolide C; Part II: Computational study on proline sulfonamide-catalyzed aldol reaction

    Creator:
    Mahapatra, Subham
    Abstract:
    More than 30 members of the diverse amphidinolide family of biologically active macrolides have been isolated over last three decades. From this family, amphidinolides C and F stand among the most complex and densely functionalized affiliates. Recently, we have accomplished the first total synthesis of amphidinolide F. The all-carbon framework...
    Resource Type:
    Dissertation
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    endeavor toward the total syntheses of amphidinolides F / C, we have uncovered a “hidden symmetry element

  • 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
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    [2.2.2]octane: A Novel C2-Symmetric Scaffold for Asymmetric Catalysis Abstract approved: James D

  • A unified approach for the total synthesis of C₁₀-functionalyzed Lycopodium alkaloids

    Creator:
    Saha, Mrinmoy
    Abstract:
    Lycopodium alkaloids have shown widespread and noteworthy biological activity, consisting of over 250 known natural products. Moreover, their structural complexity and diversity have attracted considerable attention from numerous laboratories including our own. Recently, we have developed a unified approach that would provides access to numerous, previously unprepared C₁₀-functionalized lycopodium alkaloids....
    Resource Type:
    Dissertation
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    Chemistry presented on October 29, 2014. Title: A Unified Approach for the Total Synthesis of C10

  • The development of aminal radicals for the synthesis of nitrogen-rich natural products

    Creator:
    Schiedler, David A.
    Abstract:
    Organic compounds which contain one or more nitrogen atoms are especially important as they are disproportionately represented among biologically active molecules. As a result, significant effort has been focused on the development of methods for the synthesis of nitrogenous molecules. We identified the aminal as an under-explored functional group. Despite...
    Resource Type:
    Dissertation
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    . 24 (a) Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900−5902. (b

  • Total Synthesis of Goniomitine : Development of Aminal and α-Amino Radicals in the Synthesis of Nitrogen-Rich Natural Products

    Creator:
    Vellucci, Jessica K.
    Abstract:
    Aminal radical intermediates were generated by the method of radical translocation and reacted in C-C bond forming reactions with electronically deficient alkenes (Schiedler et al. Org. Lett. 2012, 14, 6092). Aminal radical intermediates can participate in inter- and intra-molecular reactions using both Bu3SnH and (TMS)₃SiH as hydride donors. Carbon–carbon bonds...
    Resource Type:
    Dissertation
    Full Text:
    aminal bearing the nitrogen of a 2,3-disubstituted indole and the N-(2-iodobenzyl)formamide nitrogen