Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins

James A. Bull, Cristina Luján, Michael G. Hutchings, Peter Quayle

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    Abstract

    A new approach to the synthesis of the 6H-benzo[d]naphtha[1,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. © 2009 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)3617-3620
    Number of pages3
    JournalTetrahedron Letters
    Volume50
    Issue number26
    DOIs
    Publication statusPublished - 1 Jul 2009

    Keywords

    • ATRC
    • Benzannulation
    • Carbene
    • Copper
    • Cyclisation
    • Kharasch
    • Lactone
    • Radical

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