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

Hajar Baguia; Christopher Deldaele; Eugénie Romero; Bastien Michelet; Gwilherm Evano

doi:10.1055/s-0037-1610134

Synthesis, Table of Contents

Synthesis 2018; 50(15): 3022-3030
DOI: 10.1055/s-0037-1610134

special topic

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

Hajar Baguia

Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium Email: gevano@ulb.ac.be

,

Christopher Deldaele

Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium Email: gevano@ulb.ac.be

,

Eugénie Romero

Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium Email: gevano@ulb.ac.be

,

Bastien Michelet

Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium Email: gevano@ulb.ac.be

,

Gwilherm Evano *

Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium Email: gevano@ulb.ac.be

› Author Affiliations

Abstract

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Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

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 pentacyclic 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 unactivated 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.

Key words

copper catalysis - photocatalysis - radical cyclization - ynamides - cyanamides - rosettacin - luotonin A - deoxyvasicinone

Full Text

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