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

[41] Synthesis of Tetracyclic Quinazolinones Using a Visible-Light-Promoted Radical Cascade Approach [J].

Han, Yue-Yue ;

Jiang, Heng ;

Wang, Ruzhi ;

Yu, Shouyun .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :7276-7281

[42] Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine [J].

Harayama, T ;

Hori, A ;

Serban, G ;

Morikami, Y ;

Matsumoto, T ;

Abe, H ;

Takeuchi, Y .

TETRAHEDRON, 2004, 60 (47) :10645-10649

[43] A Visible-Light-Mediated Synthesis of Carbazoles [J].

Hernandez-Perez, Augusto C. ;

Collins, Shawn K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) :12696-12700

[44] Toward a Visible Light Mediated Photocyclization: Cu-Based Sensitizers for the Synthesis of [5]Helicene [J].

Hernandez-Perez, Augusto C. ;

Vlassova, Anna ;

Collins, Shawn K. .

ORGANIC LETTERS, 2012, 14 (12) :2988-2991

[45] The chemistry of amine radical cations produced by visible light photoredox catalysis [J].

Hu, Jie ;

Wang, Jiang ;

Nguyen, Theresa H. ;

Zheng, Nan .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :1977-2001

[46]

HUSAIN I, 1994, CANCER RES, V54, P539

[47] RADICAL REACTIONS IN NATURAL PRODUCT SYNTHESIS [J].

JASPERSE, CP ;

CURRAN, DP ;

FEVIG, TL .

CHEMICAL REVIEWS, 1991, 91 (06) :1237-1286

[48] Click-alkynylation of N- and P-nucleophiles by oxidative cross-coupling with alkynylcopper reagents: a general synthesis of ynamides and alkynylphosphonates [J].

Jouvin, Kevin ;

Heimburger, Jeremy ;

Evano, Gwilherm .

CHEMICAL SCIENCE, 2012, 3 (03) :756-760

[49] Copper-Catalyzed Alkynylation of Amides with Potassium Alkynyltrifluoroborates: A Room-Temperature, Base-Free Synthesis of Ynamides [J].

Jouvin, Kevin ;

Couty, Francois ;

Evano, Gwilherm .

ORGANIC LETTERS, 2010, 12 (14) :3272-3275

[50] Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives [J].

Ju, Yi ;

Liu, Feng ;

Li, Chaozhong .

ORGANIC LETTERS, 2009, 11 (16) :3582-3585

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