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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.807-815
Published online, 1st August, 2013
DOI: 10.3987/COM-13-S(S)62
Rapid and Convergent Assembly of Natural Benzo[c]phenanthridines by Palladium/Norbornene Catalysis

Pierre-Alexandre Deyris, Tatiana Caneque-Cobo, Filipe Gomes, Vanessa Narbonne, Giovanni Maestri,* and Max Malacria*

*ICNS-CNRS UPR2301, Institut Parisien De Chimie Moléculaire (IPCM), Université Pierre et Marie Curie (UPMC), 4 place Jussieu, 75252 Paris Cedex 05 Bâtiment F/74, France

Abstract

A straightforward total synthesis of a small panel of natural benzo[c]phenanthridines is described. The selective coupling of an aryl triflate with a bromobenzylamine by means of palladium/norbornene joint catalysis and a sequential transfer hydrogenation deliver these alkaloids in one pot. Dihydrophenanthridines initially formed undergo dehydrogenation smoothly while norbornene acts both as a catalyst for their assembly and as a sacrificial olefin in their dehydrogenation.