Issue 5, 2017

First total synthesis of concavine


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

Supplementary files

Article information

Article type
Edge Article
22 Dec 2016
24 Feb 2017
First published
24 Feb 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 3384-3389

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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