First total synthesis of concavine. Issue 5 (3rd March 2017)

• Record Type: Journal Article
• Authors: Saint-Dizier, François; Simpkins, Nigel S.
• Is Part Of: Chemical science. Volume 8:Issue 5(2017)
• Page Start: 3384
• Page End: 3389
• Publication Date: 2017-03-03
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6sc05627j
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : The synthesis of concavine is described, utilising a key sulfenylative radical cyclisation and highly regio- and stereocontrolled imide reactions. 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.