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

被引:41
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
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
相关论文
共 43 条
[1]   XANTHONES AND VISMIONES FROM PSOROSPERMUM-FEBRIFUGUM [J].
ABOUSHOER, M ;
SUWANBORIRUX, K ;
HABIB, AAM ;
CHANG, CJ ;
CASSADY, JM .
PHYTOCHEMISTRY, 1993, 34 (05) :1413-1420
[2]   NOVEL TETRAHYDROFUROBENZOFURANOXANTHONES FROM PSOROSPERMUM-FEBRIFUGUM [J].
ABOUSHOER, M ;
SUWANBORIRUX, K ;
CHANG, CJ ;
CASSADY, JM .
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 [J].
Arisawa, M ;
Utsumi, S ;
Nakajima, M ;
Ramesh, NG ;
Tohma, H ;
Kita, Y .
CHEMICAL COMMUNICATIONS, 1999, (05) :469-470
[5]   Efficient synthesis of (-)-trans-kumausyne via tandem intramolecular alkoxycarbonylation-lactonization [J].
Boukouvalas, J ;
Fortier, G ;
Radu, II .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :916-917
[6]   Asymmetric total synthesis of (-)-panacene and correction of its relative configuration [J].
Boukouvalas, John ;
Pouliot, Martin ;
Robichaud, Joel ;
MacNeil, Stephen ;
Snieckus, Victor .
ORGANIC LETTERS, 2006, 8 (16) :3597-3599
[7]   New oxidative transformations of phenolic and indolic oxazolines: An avenue to useful azaspirocyclic building blocks [J].
Braun, NA ;
Ousmer, M ;
Bray, JD ;
Bouchu, D ;
Peters, K ;
Peters, EM ;
Ciufolini, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4397-4408
[8]   Synthesis of spirolactams from tyrosine amides and related substances [J].
Braun, NA ;
Ciufolini, MA ;
Peters, K ;
Peters, EM .
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 [J].
BRIMBLE, MA ;
BRIMBLE, MT ;
GIBSON, JJ .
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 [J].
BRIMBLE, MA ;
STUART, SJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :881-885