Atom transfer radical cyclization of trichloroacetamides to electron-rich acceptors using Grubbs' catalysts: synthesis of the tricyclic framework of FR901483

Faïza Diaba; Agustín Martínez-Laporta; Josep Bonjoch

doi:10.1021/jo501110c

Atom transfer radical cyclization of trichloroacetamides to electron-rich acceptors using Grubbs' catalysts: synthesis of the tricyclic framework of FR901483

J Org Chem. 2014 Oct 3;79(19):9365-72. doi: 10.1021/jo501110c. Epub 2014 Sep 18.

Authors

Faïza Diaba¹, Agustín Martínez-Laporta, Josep Bonjoch

Affiliation

¹ Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB, Universitat de Barcelona , Av. Joan XXIII s/n, 08028-Barcelona, Spain.

PMID: 25203675
DOI: 10.1021/jo501110c

Abstract

Intramolecular Kharasch-type additions of trichloroacetamides on anisole and enol acetates catalyzed by Grubbs' ruthenium carbenes are described. This protocol provides access to highly functionalized 2-azaspiro[4.5]decanes, morphan compounds, and the azatricyclic core of FR901483.