Microwave-enhanced synthesis of N-shifted buflavine analogues via a Suzuki-ring-closing metathesis protocol

被引：68

作者：

Appukkuttan, P ^{[1
]}

Dehaen, W ^{[1
]}

Van der Eycken, E ^{[1
]}

机构：

[1] Univ Louvain, Dept Chem, B-3001 Heverlee, Belgium

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol050806+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel, microwave-enhanced six-step synthesis was devised for the synthesis of N-shifted buflavine analogues. Microwave-enhanced Suzuki-Miyaura cross-coupling and ring-closing metathesis reactions were used as the key steps. Microwave irradiation was found to enhance the ring-closing metathesis reaction to generate the otherwise difficulty obtainable medium-sized ring system of the target molecules.

引用

页码：2723 / 2726

页数：4

共 53 条

[1] The directed ortho metalation -: cross coupling symbiosis.: Regioselective methodologies for biaryls and heterobiaryls.: Deployment in aromatic and heteroaromatic natural product synthesis
Anctil, EJG
Snieckus, V
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) : 150 - 160
[2] Microwave-enhanced cadogan cyclization: An easy access to the 2-substituted carbazoles and other fused heterocyclic systems
Appukkuttan, P
Van der Eycken, E
Dehaen, W
[J]. SYNLETT, 2005, (01) : 127 - 133
[3] Generation of a small library of highly electron-rich 2-(Hetero)aryl-substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue
Appukkuttan, P
Orts, AB
Chandran, RP
Goeman, JL
Van der Eycken, J
Dehaen, W
Van der Eycken, E
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) : 3277 - 3285
[4] Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams
Banfi, L
Basso, A
Guanti, G
Riva, R
[J]. TETRAHEDRON LETTERS, 2003, 44 (41) : 7655 - 7658
[5] Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams
Baudoin, O
Cesario, M
Guénard, D
Guéritte, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) : 1199 - 1207
[6] Blackwell HE, 1998, ANGEW CHEM INT EDIT, V37, P3281, DOI 10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0.CO
[7] 2-V
[8] The directed ortho metalation-transition metal-catalyzed reaction symbiosis in heteroaromatic synthesis
Chauder, B
Green, L
Snieckus, V
[J]. PURE AND APPLIED CHEMISTRY, 1999, 71 (08) : 1521 - 1529
[9] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
Deiters, A
Martin, SF
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
[10] Total syntheses of the phytotoxic lactones herbarumin I and II and a synthesis-based solution of the pinolidoxin puzzle
Fürstner, A
Radkowski, K
Wirtz, C
Goddard, R
Lehmann, CW
Mynott, R
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) : 7061 - 7069

← 1 2 3 4 5 6 →