Expedient Pd‐Catalyzed α‐Arylation towards Dibenzoxepinones. Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids
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Authors
Deichert, Julie Amanda
Mizufune, Hideya
Patel, Jignesh J.
Hurst, Timothy E.
Maheta, Ashish
Kitching, Matthew
Ross, Avena
Snieckus, Victor
Date
2020-04-03
Type
journal article
Language
en
Keyword
Alkaloids , Arylation , Homogeneous Catalysis , Nitrogen Heterocycles , Palladium , Synthetic Methods
Alternative Title
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.
Description
This is the peer reviewed version of the following article: Deichert, J.A., Mizufune, H., Patel, J.J., Hurst, T.E., Maheta, A., Kitching, M.O., Ross, A.C. and Snieckus, V. (2020), Expedient Pd‐Catalyzed α‐Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids. Eur. J. Org. Chem.. doi:10.1002/ejoc.202000424, which has been published in final form at https://doi.org/10.1002/ejoc.202000424. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Citation
Deichert, J.A., Mizufune, H., Patel, J.J., Hurst, T.E., Maheta, A., Kitching, M.O., Ross, A.C. and Snieckus, V. (2020), Expedient Pd‐Catalyzed α‐Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids. Eur. J. Org. Chem.. doi:10.1002/ejoc.202000424
Publisher
Wiley