• Login
    View Item 
    •   Shocker Open Access Repository Home
    • Fairmount College of Liberal Arts and Sciences
    • Chemistry and Biochemistry
    • CHEM Faculty Scholarship
    • CHEM Faculty Publications
    • View Item
    •   Shocker Open Access Repository Home
    • Fairmount College of Liberal Arts and Sciences
    • Chemistry and Biochemistry
    • CHEM Faculty Scholarship
    • CHEM Faculty Publications
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    A convenient entry to C2- and C3-substituted gulono-gamma-lactone derivatives from L-ascorbic acid

    Date
    2005-08-19
    Author
    Olabisi, Ayodele O.
    Mahindaratne, Mathew P. D.
    Wimalasena, Kandatege
    Metadata
    Show full item record
    Citation
    The Journal of organic chemistry. 2005 Aug 19; 70(17): 6782-9.
    Abstract
    A convenient method to obtain unknown chiral C2- and C3-functionalized aldono-1,4-lactone derivatives starting from l-ascorbic acid, which would be valuable in the synthesis of derivatives of various pharmacologically active agents for structure-activity studies, is described. The practicality of this approach is demonstrated by the synthesis of a series of 5,6-O-isopropylidene-2-allyl-3-keto-l-galactono-gamma-lactone and 5,6-O-isopropylidene-3-allyl-2-keto-l-galactono-gamma-lactone derivatives using the thermal Claisen rearrangement of the corresponding 3-O- and 2-O-allyl derivatives of 5,6-O-isopropylidene-l-ascorbic acid, respectively, followed by stereospecific reduction to the corresponding alcohols. The synthetic steps are shown to be efficient, and enantiospecific, and they proceed with high yields.
    Description
    Click on the DOI link below to access the article (may not be free).
    URI
    http://dx.doi.org/10.1021/jo0508550
    http://hdl.handle.net/10057/4294
    Collections
    • CHEM Faculty Publications

    Browse

    All of Shocker Open Access RepositoryCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsBy TypeThis CollectionBy Issue DateAuthorsTitlesSubjectsBy Type

    My Account

    LoginRegister

    Statistics

    Most Popular ItemsStatistics by CountryMost Popular Authors

    DSpace software copyright © 2002-2023  DuraSpace
    DSpace Express is a service operated by 
    Atmire NV