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Total Synthesis of Iso- and Bongkrekic Acids: Natural Antibiotics Displaying Potent Antiapoptotic Properties

Authors

  • Dr. Antoine Français,

    Corresponding author
    1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW Cambridge (UK), Fax: (+44) 1223-336-442
    • Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW Cambridge (UK), Fax: (+44) 1223-336-442
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  • Dr. Antonio Leyva-Pérez,

    1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW Cambridge (UK), Fax: (+44) 1223-336-442
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  • Dr. Gorka Etxebarria-Jardi,

    1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW Cambridge (UK), Fax: (+44) 1223-336-442
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  • Javier Peña,

    1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW Cambridge (UK), Fax: (+44) 1223-336-442
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  • Prof. Dr. Steven V. Ley

    Corresponding author
    1. Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW Cambridge (UK), Fax: (+44) 1223-336-442
    • Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW Cambridge (UK), Fax: (+44) 1223-336-442
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Abstract

For over five decades, owing to their antiapoptotic activities, bongkrekic and isobongkrekic acids have generated interest from the scientific community. Here, we disclose full details of our investigation into the synthesis of isobongkrekic acid, which culminated in its first preparation and features various palladium-catalysed cross-couplings and Takai olefination reactions. Access to bongkrekic acid is also reported by this route. These syntheses involve the preparation and use of new general building blocks which could find wider applications.

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