• Login
    View Item 
    •   Home
    • Brock Theses
    • Newly Added Theses
    • View Item
    •   Home
    • Brock Theses
    • Newly Added Theses
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of BrockUCommunitiesPublication DateAuthorsTitlesSubjectsThis CollectionPublication DateAuthorsTitlesSubjectsProfilesView

    My Account

    LoginRegister

    Statistics

    Display statistics

    Synthesis of C-1 Homologues of Narciclasine

    • CSV
    • RefMan
    • EndNote
    • BibTex
    • RefWorks
    Thumbnail
    Name:
    BROCK_HABAZ_LIHI_2022.pdf
    Size:
    5.795Mb
    Format:
    PDF
    Download
    Author
    Habaz, Lihi
    Keyword
    biocatalysis, narciclasine, pancratistatin, chemoenzymatic, natural products, total synthesis
    
    Metadata
    Show full item record
    URI
    http://hdl.handle.net/10464/16870
    Abstract
    This thesis describes current progress towards the total synthesis of C1-homologues of the Amaryllidaceae alkaloid narciclasine (1), a powerful anticancer agent which suffers from a poor solubility profile. A 15-step chemoenzymatic total synthesis of C-1 carboxymethyl narciclasine (248) was accomplished. A key step in this convergent synthesis is the formation of the C ring syn-diol moiety via the chemoenzymatic dihydroxylation of ortho-dibromobenzene to provide the corresponding cis-dihydrodiene diol as a single enantiomer, which constitutes an efficient method of generating chiral substrates from readily available commercial materials. The dense A ring functionalities are derived from another commercially available unit; ortho-vanillin, via previously established protocols. Further key steps involve a nitroso Diels-Alder reaction and an intramolecular Heck reaction. The C-1 homologue that was prepared, 248, was then tested for its biological activity against natural narciclasine as the positive control. Experimental and spectral data are provided for all novel compounds.
    Collections
    Newly Added Theses

    entitlement

     
    DSpace software (copyright © 2002 - 2023)  DuraSpace
    Quick Guide | Contact Us
    Open Repository is a service operated by 
    Atmire NV
     

    Export search results

    The export option will allow you to export the current search results of the entered query to a file. Different formats are available for download. To export the items, click on the button corresponding with the preferred download format.

    By default, clicking on the export buttons will result in a download of the allowed maximum amount of items.

    To select a subset of the search results, click "Selective Export" button and make a selection of the items you want to export. The amount of items that can be exported at once is similarly restricted as the full export.

    After making a selection, click one of the export format buttons. The amount of items that will be exported is indicated in the bubble next to export format.