• Login
    View Item 
    •   SMARTech Home
    • Georgia Tech Theses and Dissertations
    • Georgia Tech Theses and Dissertations
    • View Item
    •   SMARTech Home
    • Georgia Tech Theses and Dissertations
    • Georgia Tech Theses and Dissertations
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Intramolecular cyclization strategies for synthesizing medium-ring polycycles and the total synthesis of natural products

    Thumbnail
    View/Open
    patil_dadasaheb_v_201212_phd.pdf (12.28Mb)
    Date
    2012-08-16
    Author
    Patil, Dadasaheb V.
    Metadata
    Show full item record
    Abstract
    Carbo- and heterocyclic compounds are of great interest to chemists. Intramolecular cyclization strategies of donor-acceptor (D-A) cyclopropanes and alkylidene malonate monoamides have excellent potential for synthesis as they offer easy access to structurally-diverse compounds. The work described in this thesis accesses the scope of the In(OTf)3-catalyzed cyclization reaction of cyclopropanes and alkylidene malonate monoamides. In(OTf)3-catalyzed reactions of alkenyl and heteroaryl cyclopropyl ketones were examined in the synthesis of functionalized cyclohexenone-based derivatives (Chapter 2). Subsequent efforts to utilize a tandem cyclopropane ring-opening/Friedel-Crafts alkylation sequence of methyl 1-(1H-indolecarbonyl)-1-cyclopropanecarboxylates to prepare functionalized hydropyrido[1,2-a]indole-6(7H)-ones is discussed in Chapter 3. The extension of this tandem protocol towards the total synthesis of (±)-deethyleburnamonine is the subject of Chapter 6. Intramolecular Friedel-Crafts alkylation of N-indolyl alkylidene malonate monoamides was also examined. An In(OTf)3-catalyzed cyclization of substituted methyl 2-(1H-indole-1-carbonyl) acrylates afforded a series of 1H-pyrrolo[1,2-a]indole-3(2H)-ones (Chapter 4), whereas substrates with the indole 2-position blocked provided access to substituted 4H-pyrrolo[3,2,1-ij]quinolin-4-ones (Chapter 5).
    URI
    http://hdl.handle.net/1853/50118
    Collections
    • Georgia Tech Theses and Dissertations [22398]
    • School of Chemistry and Biochemistry Theses and Dissertations [1461]

    Browse

    All of SMARTechCommunities & CollectionsDatesAuthorsTitlesSubjectsTypesThis CollectionDatesAuthorsTitlesSubjectsTypes

    My SMARTech

    Login

    Statistics

    View Usage StatisticsView Google Analytics Statistics
    • About
    • Terms of Use
    • Contact Us
    • Emergency Information
    • Legal & Privacy Information
    • Accessibility
    • Accountability
    • Accreditation
    • Employment
    • Login
    Georgia Tech

    © Georgia Institute of Technology

    • About
    • Terms of Use
    • Contact Us
    • Emergency Information
    • Legal & Privacy Information
    • Accessibility
    • Accountability
    • Accreditation
    • Employment
    • Login
    Georgia Tech

    © Georgia Institute of Technology