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Issue 5, 2017
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First total synthesis of concavine

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Abstract

The synthesis of the unusual alkaloid concavine, isolated from Clitocybe concava (Basidiomycetae), has been accomplished. The synthetic route features regio- and stereoselective manipulation of polycyclic imide intermediates via enolate substitution and Grignard addition, along with a key bridge-forming step involving a new method for sulfenylative radical cyclisation. The NMR data for synthetic concavine demonstrate that the original data reported for the natural product refer to the derived acetic acid salt, probably formed as an artefact of isolation or purification.

Graphical abstract: First total synthesis of concavine

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Publication details

The article was received on 22 Dec 2016, accepted on 24 Feb 2017 and first published on 24 Feb 2017


Article type: Edge Article
DOI: 10.1039/C6SC05627J
Citation: Chem. Sci., 2017,8, 3384-3389
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    First total synthesis of concavine

    F. Saint-Dizier and N. S. Simpkins, Chem. Sci., 2017, 8, 3384
    DOI: 10.1039/C6SC05627J

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