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    Expedient Pd‐Catalyzed α‐Arylation towards Dibenzoxepinones. Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids

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    Date
    2020-04-03
    Author
    Deichert, Julie Amanda
    Mizufune, Hideya cc
    Patel, Jignesh J.
    Hurst, Timothy E.
    Maheta, Ashish
    Kitching, Matthew
    Ross, Avena
    Snieckus, Victor
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    Abstract
    The general synthesis of diversely substituted dibenzoxepinones by a combined Pd‐catalyzed α‐arylation and SNAr strategy is reported and applied to the synthesis of Manske's ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α‐arylation reaction.
    URI for this record
    http://hdl.handle.net/1974/27821
    External DOI
    https://doi.org/10.1002/ejoc.202000424
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    • Department of Chemistry Faculty Publications
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