Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic Nucleosides

Neogi, Arpita and Majhi, Tirtha Pada and Mukhopadhyay, Ranjan and Chattopadhyay, Partha (2006) Palladium-Mediated Intramolecular Aryl Amination on Furanose Derivatives: An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic Nucleosides. The Journal of Organic Chemistry, 71. pp. 3291-3294.

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    Abstract

    Pd-catalyzed intramolecular arylamination on sugar derivatives has been accomplished by using bulky biaryl phosphine ligands. An application of this methodology on a variety of D-glucose-derived substrates, 2a-f, led to the synthesis of highly functionalized cis-fused tricyclic oxazocines, 3a-e. The products could subsequently be transformed to the optically active benzoxazocine derivative 4 and tricyclic nucleoside 6. This is the first example of the synthesis of eight-membered rings via intramolecular cycloamination of furanose derivatives, which provides a very useful method for the catalytic synthesis of medium-ring heterocycles

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/400
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Ms Sutapa Ganguly
    Date Deposited: 31 Oct 2011 16:44
    Last Modified: 03 Feb 2012 12:46
    Official URL: http://dx.doi.org/10.1021/jo052420i CCC: $33.50
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