Sequential Baylis–Hillman Reaction and Radical Cyclization of Furanose Derivatives: Expeditious Approach to Enantiopure Benzo-Fused Nine-Membered Oxacycles

Majhi, Tirtha Pada and Neogi, Arpita and Ghosh, Soumen and Mukherjee, Alok Kumar and Chattopadhyay, Partha (2006) Sequential Baylis–Hillman Reaction and Radical Cyclization of Furanose Derivatives: Expeditious Approach to Enantiopure Benzo-Fused Nine-Membered Oxacycles. Tetrahedron, 62 (51). pp. 12003-12010.

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    Abstract

    A regioselective 9-endo-trig aryl radical cyclization of D-glucose derived diastereomeric Baylis–Hillman reaction products with Bu3SnH led to highly functionalized tricyclic benzannulated ethers incorporating cis- and trans-9,5 bicyclic systems in good yields. Degradation of one of the products afforded an enantiopure multifunctionalized benzoxonine derivative.

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/1090
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Mr Santanu Sadhukhan
    Date Deposited: 28 Dec 2011 17:30
    Last Modified: 03 Feb 2012 12:24
    Official URL: http://dx.doi.org/10.1016/j.tet.2006.09.080
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