Synthesis 2018; 50(15): 3022-3030
DOI: 10.1055/s-0037-1610134
special topic
© Georg Thieme Verlag Stuttgart · New York

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
,
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
This work was supported by the Université libre de Bruxelles (ULB) and the Fédération Wallonie-Bruxelles (ARC Consolidator 2014-2019). H. B. and C. D. acknowledge the Fonds pour la formation à la Recherche dans l’Industrie et dans l’Agriculture (F.R.I.A.) for graduate fellowships.
Further Information

Publication History

Received: 09 March 2018

Accepted after revision: 09 April 2018

Publication Date:
28 May 2018 (online)

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.

Supporting Information

 
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