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Copper-Catalyzed Photoinduced Radical Domino Cyclization of Ynamides and Cyanamides: a Unified Entry to Rosettacin, Luotonin A and Deoxyvasicinone

par Baguia, Hajar ;Deldaele, Christopher ;Romero, Eugénie ;Michelet, Bastien ;Evano, Gwilherm
Référence Synthesis, 50, page (3022-3030)
Publication Publié, 2018

Article révisé par les pairs

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Résumé :

A general and efficient procedure for the copper-catalyzed photoinduced radical domino cyclization of ynamides and cyanamides providing an efficient access to complex tri-, tetra- and penta- cyclic nitrogen heterocycles is reported. Upon visible light irradiation in the presence of catalytic amounts of [(DPEphos)(bcp)Cu]PF6 and an amine, a range of unac-tivated aryl and alkyl iodides were shown to be smoothly transformed to the corresponding radical species, initiating the radical domino cyclization. This procedure provides a unified entry to rosettacin, luotonin A and deoxyvasicinone that could be efficiently prepared in a limited number of steps.