An expeditious synthesis of polyhydroxylated 2-arylbenzo[b]furans

被引：27

作者：

Dupont, R ^{[1
]}

Cotelle, P ^{[1
]}

机构：

[1] Univ Lille 1, ENSCL, CNRS, Chim Organ Phys Lab, F-59655 Villeneuve Dascq, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 26期

关键词：

boron and compounds; dealkylation; cyclisation; benzofurans;

D O I：

10.1016/S0040-4020(01)00462-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expeditious synthesis of polyhydroxylated 2-arylbenzo[b]furans is described. The key steps are the conversion of the corresponding polymethoxylated stilbenes into diarylethanoid molecules (epoxide or alcohol) that were demethylated and cyclised using boron tribromide to give the target polyhydroxylated 2-arylbenzo[b]furans. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5585 / 5589

页数：5

共 28 条

[1]

ALI MA, 1992, CHEM PHARM BULL, V40, P1130, DOI 10.1248/cpb.40.1130

[2] SIMPLE PROCEDURE FOR EPOXIDATION OF ACID-SENSITIVE OLEFINIC COMPOUNDS WITH META-CHLOROPERBENZOIC ACID IN AN ALKALINE BIPHASIC SOLVENT SYSTEM [J].

ANDERSON, WK ;

VEYSOGLU, T .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12) :2267-2268

[3]

ANJANEYULU ASR, 1990, INDIAN J CHEM B, V29, P219

[4] PHENOL OXIDATION .4. SYNTHESIS AND NOVEL RING-OPENING OF SPIROCYCLIC DIENONES RELATED TO BENZYLISOQUINOLINE ALKALOID COUMARINE [J].

BIRCH, AJ ;

JACKSON, AH ;

SHANNON, PVR ;

STEWART, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (23) :2492-2501

[5] THE CHEMISTRY OF THE INSOLUBLE RED WOODS .7. THE SYNTHESIS OF COUMARINO(3'-4'-3-2)COUMARONES [J].

BOWYER, WJ ;

ROBERTSON, A ;

WHALLEY, WB .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (FEB) :542-544

[6] LITHIATED CARBANIONS OF BETA, GAMMA-UNSATURED ALPHA'-CYANOETHERS .4. [2.3] SIGMATROPIC REARRANGEMENTS IN BENZYLIC SERIES - ORTHO-METHYLARYL KETONES [J].

CAZES, B ;

JULIA, S .

TETRAHEDRON, 1979, 35 (22) :2655-2660

[7] SUBSTITUTED (1,2-DIARYLETHYL)AMIDE ACYL-COA-CHOLESTEROL ACYLTRANSFERASE INHIBITORS - EFFECT OF POLAR GROUPS ON IN-VITRO AND IN-VIVO ACTIVITY [J].

CLADER, JW ;

BERGER, JG ;

BURRIER, RE ;

DAVIS, HR ;

DOMALSKI, M ;

DUGAR, S ;

KOGAN, TP ;

SALISBURY, B ;

VACCARO, W .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (10) :1600-1607

[8] 1,2-DISUBSTITUTED ETHANES AS POSSIBLE PRECURSORS FOR THE SYNTHESIS OF CANNABIS SPIRANS [J].

CROMBIE, L ;

CROMBIE, WML ;

JAMIESON, SV ;

TUCHINDA, P ;

WHITAKER, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (07) :1485-1491

[9] The total synthesis of salvianolic acid F [J].

Dalla, V ;

Cotelle, P .

TETRAHEDRON, 1999, 55 (22) :6923-6930

[10] Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide [J].

Dupont, R ;

Cotelle, P .

TETRAHEDRON LETTERS, 2001, 42 (04) :597-600

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