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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:
    describes the enantioselective hetero-Diels-Alder (HDA) reaction of Danishefsky diene with a large number

  • Total Synthesis of Aspidosperma Alkaloids Leuconoxine, Melodinine E and Mersicarpine and Synthetic Studies directed toward the Iboga Alkaloid Ibogaine: Progress directed toward the dimeric Cephalotaxus Alkaloid Cephalancetine C

    Creator:
    Kim, GilSoo
    Abstract:
    The first part of this manuscript is about the total synthesis of the aspidosperma alkaloids leuconoxine, melodinine E and mersicarpine. Our synthetic strategy used a radical translocation-conjugate addition cascade to construct the core of the natural product. Specifically, a vinyl radical was generated from the homolysis of the C–I bond...
    Resource Type:
    Dissertation
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    iboga alkaloid ibogaine. Our initial strategy used the tandem radical 6-exo-trig/5-exo-trig

  • 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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    ....................................................................................................... 127 Chapter 6: Studies Towards Eastern Half of Himeradine A

  • 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
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    Section…………………………………………………….. References………………………………………………………………... Page 186 190 233 CHAPTER 6

  • Computational Investigation and Prediction of Mechanisms and Stereocontrol in Complex Organic Reactions

    Creator:
    Pattawong, Ommidala
    Abstract:
    Complex organic transformations, such as the addition of pyrrole to ketene using planar chiral organocatalyst (*PPY), the four-component anhydride- Manniach reactions, and the site-selective desymmetrization of meso-1,2-diol, are remarkable synthetic reactions that provide high yield and high selectivity. However, the exact mechanism and origins of stereocontrol for theses synthetic organic...
    Resource Type:
    Dissertation
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    preparation and review of this manuscript. Chapter 6. Paul Ha-Yeon Cheong contributed in part to the

  • 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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    ……..………..………..………..………..………..…...5 1.4. Synthetic studies……..………..………..………..………..………..………..…...6 1.4.1. Danishefsky’s total

  • Bioprospecting the Chemical Diversity of Plant-associated Fungi

    Creator:
    González-Montiel, Gisela Abigail
    Abstract:
    Fungi have long been used for discovery of new chemical scaffolds. In the clinical setting, the fungal natural products penicillin, statins, and cyclosporine have revolutionized medicine to treat diseases and infections. In the environment, fungal natural products have been used as herbicides, fungicides, and insecticides to protect crops, livestock, and...
    Resource Type:
    Masters Thesis
    Full Text:
    ……............................…………………………………...2 1.3 Fungi and fungal natural products ...................................…………….…....6 1.4

  • 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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    Experimental…...……………………………..…… 138 TABLE OF CONTENTS (Continued) Page CHAPTER 6 SYNTHESIS

  • Drug Discovery from Diverse Bacteria – Bioactivity-guided Isolation of Known and New Metabolites

    Creator:
    Zhu, Chenxi
    Abstract:
    Exploring bioactive natural products has contributed largely to clinically approved drugs we have been using over the last 100 years. Especially among the anti-infective drugs, around 70% of currently used antibiotics were discovered or derived from microbial secondary metabolites, among them compounds like vancomycin, chloramphenicol, and erythromycin. Facing the unavoidable...
    Resource Type:
    Dissertation
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    .............................................................. 6 Figure 2.1 Collection of the bacterial strain library of Loesgen Lab

  • Total Synthesis of Cephalotaxus Alkaloids and Synthetic Studies toward Bazzanin K

    Creator:
    Ju, Xuan
    Abstract:
    Dearomatization reactions exist broadly in biosynthesis and chemical synthesis. The highly functionalized atoms of arenes can be masked by it aromaticity, and upon dearomatization, those reactive atoms can be readily applied to bond formation and further manipulation. The total synthesis of (–)-cephalotaxine and (–)- homoharringtonine is described via an oxidative...
    Resource Type:
    Dissertation
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    …………………………………………………………...105 6 Summary and Furture Work……………………………………………………...139 LIST OF FIGURES