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

被引：51

作者：

Baguia, Hajar ^{[1
]}

Deldaele, Christopher ^{[1
]}

Romero, Eugenie ^{[1
]}

Michelet, Bastien ^{[1
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Serv Chim & Physicochim Organ, Lab Chim Organ, Ave FD Roosevelt 50,CP160-06, B-1050 Brussels, Belgium

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 15期

关键词：

copper catalysis; photocatalysis; radical cyclization; ynamides; cyanamides; rosettacin; luotonin A; deoxyvasicinone; TOPOISOMERASE-I INHIBITORS; LIGHT PHOTOREDOX CATALYSIS; RHODIUM(III)-CATALYZED INTRAMOLECULAR ANNULATION; VISIBLE-LIGHT; NATURAL-PRODUCTS; FACILE SYNTHESIS; ALKYNYLCOPPER REAGENTS; OXIDATIVE ALKYNYLATION; CAMPTOTHECA-ACUMINATA; NITROGEN NUCLEOPHILES;

D O I：

10.1055/s-0037-1610134

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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]PF (6) 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.

引用

页码：3022 / 3030

页数：9

共 114 条

[1] TRANSITION-METAL COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION - SYNTHESIS OF 4(3H)-QUINAZOLINONE DERIVATIVES FROM N-(2-NITROBENZOYL)AMIDES [J].