Novel formal [2+3] cycloaddition between substituted phenols and furan

被引：40
作者：
Berard, Didier [1 ]
Jean, Alexandre [1 ]
Canesi, Sylvain [1 ]
机构：
[1] Univ Quebec, Lab Methodol & Synth Prod Nat, Montreal, PQ H3C 3P8, Canada
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 46期
关键词：
hypervalent iodine; furan; phenols; cycloaddition [2+3;
D O I：
10.1016/j.tetlet.2007.09.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of various substituted phenols in the presence of furan, iodobenzene diacetate, and trifluoroethanol promotes oxidative formal [2+3] cycloaddition in moderate to useful yields. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8238 / 8241
页数：4
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共 43 条
  • [1] XANTHONES AND VISMIONES FROM PSOROSPERMUM-FEBRIFUGUM
    ABOUSHOER, M
    SUWANBORIRUX, K
    HABIB, AAM
    CHANG, CJ
    CASSADY, JM
    [J]. PHYTOCHEMISTRY, 1993, 34 (05) : 1413 - 1420
  • [2] NOVEL TETRAHYDROFUROBENZOFURANOXANTHONES FROM PSOROSPERMUM-FEBRIFUGUM
    ABOUSHOER, M
    SUWANBORIRUX, K
    CHANG, CJ
    CASSADY, JM
    [J]. TETRAHEDRON LETTERS, 1989, 30 (26) : 3385 - 3388
  • [3] Akai S, 2002, HETEROCYCLES, V58, P75
  • [4] An unexpected intermolecular chiral biaryl coupling reaction induced by a hypervalent iodine(III) reagent: synthesis of potential precursor for ellagitannin
    Arisawa, M
    Utsumi, S
    Nakajima, M
    Ramesh, NG
    Tohma, H
    Kita, Y
    [J]. CHEMICAL COMMUNICATIONS, 1999, (05) : 469 - 470
  • [5] Efficient synthesis of (-)-trans-kumausyne via tandem intramolecular alkoxycarbonylation-lactonization
    Boukouvalas, J
    Fortier, G
    Radu, II
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) : 916 - 917
  • [6] Asymmetric total synthesis of (-)-panacene and correction of its relative configuration
    Boukouvalas, John
    Pouliot, Martin
    Robichaud, Joel
    MacNeil, Stephen
    Snieckus, Victor
    [J]. ORGANIC LETTERS, 2006, 8 (16) : 3597 - 3599
  • [7] New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building blocks
    Braun, NA
    Ousmer, M
    Bray, JD
    Bouchu, D
    Peters, K
    Peters, EM
    Ciufolini, MA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) : 4397 - 4408
  • [8] Synthesis of spirolactams from tyrosine amides and related substances
    Braun, NA
    Ciufolini, MA
    Peters, K
    Peters, EM
    [J]. TETRAHEDRON LETTERS, 1998, 39 (26) : 4667 - 4670
  • [9] SYNTHESIS OF THE CIS-3A,8B-DIHYDROFURO[3,2-B]BENZOFURAN-2(3H)-ONE RING-SYSTEM VIA A FUROFURAN ANNULATION TO ACTIVATED BENZOQUINONES
    BRIMBLE, MA
    BRIMBLE, MT
    GIBSON, JJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01): : 179 - 184
  • [10] SYNTHESIS OF 5-EPI-7-DEOXYKALAFUNGIN AND 5-EPI-7-O-METHYLKALAFUNGIN
    BRIMBLE, MA
    STUART, SJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04): : 881 - 885
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