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
Authors
Deichert, Julie Amanda
Mizufune, Hideya
Patel, Jignesh J.
Hurst, Timothy E.
Maheta, Ashish
Kitching, Matthew
Ross, Avena
Snieckus, Victor
Keyword
Alkaloids , Arylation , Homogeneous Catalysis , Nitrogen Heterocycles , Palladium , Synthetic Methods
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.