Microwave-enhanced synthesis of new (-)-steganacin and (-)-steganone aza analogues

被引:43
作者
Beryozkina, T [1 ]
Appukkuttan, P [1 ]
Mont, N [1 ]
Van der Eycken, E [1 ]
机构
[1] Univ Louvain, Dept Chem, B-3001 Louvain, Belgium
关键词
D O I
10.1021/ol052766f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel, microwave-enhanced, highly efficient protocol for the synthesis of hitherto unknown (-)-steganacin and (-)-steganone 7-aza analogues containing a 1,2,3-triazole ring has been presented. Microwave irradiation was found to be highly beneficial in promoting the Suzuki reaction and the 1,3-dipolar cycloaddition reaction to generate the highly strained medium-sized ring system of the title molecules.
引用
收藏
页码:487 / 490
页数:4
相关论文
共 41 条
[1]   TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].
APPEL, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811
[2]   Microwave-enhanced synthesis of N-shifted buflavine analogues via a Suzuki-ring-closing metathesis protocol [J].
Appukkuttan, P ;
Dehaen, W ;
Van der Eycken, E .
ORGANIC LETTERS, 2005, 7 (13) :2723-2726
[3]   Microwave-enhanced cadogan cyclization: An easy access to the 2-substituted carbazoles and other fused heterocyclic systems [J].
Appukkuttan, P ;
Van der Eycken, E ;
Dehaen, W .
SYNLETT, 2005, (01) :127-133
[4]   A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction [J].
Appukkuttan, P ;
Dehaen, W ;
Fokin, VV ;
Van der Eycken, E .
ORGANIC LETTERS, 2004, 6 (23) :4223-4225
[5]   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 [J].
Appukkuttan, P ;
Orts, AB ;
Chandran, RP ;
Goeman, JL ;
Van der Eycken, J ;
Dehaen, W ;
Van der Eycken, E .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) :3277-3285
[6]  
Biagi Giuliana, 2004, Farmaco (Lausanne), V59, P397, DOI 10.1016/j.farmac.2004.01.012
[7]   RUTHENIUM DIOXIDE IN FLUORO ACID-MEDIUM .5. APPLICATION TO THE NON PHENOLIC OXIDATIVE COUPLING OF DIARYLBUTANES - CONFORMATIONAL STUDIES OF CIS AND TRANS DEOXYSCHIZANDRINS [J].
DHAL, R ;
LANDAIS, Y ;
LEBRUN, A ;
LENAIN, V ;
ROBIN, JP .
TETRAHEDRON, 1994, 50 (04) :1153-1164
[8]  
Diederich F., 1998, METAL CATALYZED CROS, P517
[9]   Asymmetric 1,3-dipolar cycloaddition reactions [J].
Gothelf, KV ;
Jorgensen, KA .
CHEMICAL REVIEWS, 1998, 98 (02) :863-909
[10]   Stereoselective synthesis of axially chiral natural products, (-)-steganone and O,O′-dimethylkorupensamine A, utilizing planar chiral (arene)chromium complexes [J].
Kamikawa, K ;
Watanabe, T ;
Daimon, A ;
Uemura, M .
TETRAHEDRON, 2000, 56 (15) :2325-2337