The first total synthesis of Cicerfuran utilizing a one-pot synthesis of hydroxylated benzofurans

被引:49
作者
Novák, Z [1 ]
Timári, G [1 ]
Kotschy, A [1 ]
机构
[1] Eotvos Lorand Univ, Dept Gen & Inorgan Chem, H-1117 Budapest, Hungary
关键词
cross-coupling; benzofurane; natural product;
D O I
10.1016/S0040-4020(03)01170-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple one-pot procedure was elaborated for the preparation of hydroxylated benzofurans from halogenated phenols and was successfully applied to the first total synthesis of Cicerfuran, a natural defence agent of wild chickpea. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7509 / 7513
页数:5
相关论文
共 23 条
[1]  
ALEWANDER BH, 1958, J ORG CHEM, V23, P1969
[2]  
Arcadi A, 2002, SYNLETT, P453
[3]   Palladium-catalyzed reaction of o-ethynylphenols, o-((trimethylsilyl)ethynyl)phenyl acetates, and o-alkynylphenols with unsaturated triflates or halides: A route to 2-substituted-, 2,3-disubstituted-, and 2-substituted-3-acylbenzo[b]furans [J].
Arcadi, A ;
Cacchi, S ;
DelRosario, M ;
Fabrizi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9280-9288
[4]   A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions [J].
Chow, HF ;
Wan, CW ;
Low, KH ;
Yeung, YY .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1910-1913
[5]   SYNTHESIS OF COUMESTROL, 3,9-DIHYDROXY-6H-BENZOFURO[3,2-C][1]BENZOPYRAN-6-ONE [J].
EMERSON, OH ;
BICKOFF, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (16) :4381-4383
[6]  
Friedrichsen W., 1996, Comprehensive Heterocyclic Chemistry II, V2, P351
[7]   Total syntheses of three natural products, vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol from a common starting material [J].
Hiroya, K ;
Suzuki, N ;
Yasuhara, A ;
Egawa, Y ;
Kasano, A ;
Sakamoto, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (24) :4339-4346
[8]   Pd(PhCN)2Cl2/P(t-Bu)3:: A versatile catalyst for sonogashira reactions of aryl bromides at room temperature [J].
Hundertmark, T ;
Littke, AF ;
Buchwald, SL ;
Fu, GC .
ORGANIC LETTERS, 2000, 2 (12) :1729-1731
[9]   Furano-compounds part III euparan [J].
Kamthong, B ;
Robertson, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :925-930
[10]  
Keay B.A., 1997, Comprehensive Heterocyclic Chemistry II, V2, P395, DOI DOI 10.1016/B978-008096518-5.00047-2