A new approach to 2-aryl-7-alkoxy-benzofurans: Synthesis of ailanthoidol, a natural neolignan

被引:48
作者
Fuganti, C [1 ]
Serra, S [1 ]
机构
[1] Ctr CNR Chim Sostanze Organiche Nat, Dipartimento Chim Politecn, I-20131 Milan, Italy
关键词
annulation; benzofurans; lignans; natural products;
D O I
10.1016/S0040-4039(98)01053-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general method of synthesis of 2-aryl-7-alkoxy-benzofurans is described using a benzoannulation reaction as key step. The usefulness of this approach is shown in the new synthesis of ailanthoidol, a benzofuranoid neolignan isolated from the tree Zanthoxylum ailanthoides. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5609 / 5610
页数:2
相关论文
共 11 条
[1]   Recent progress on the iterative construction of 4-substituted-3-hydroxy benzoic acids from unsaturated aldehydes and dimethyl succinate [J].
Brenna, E ;
Fuganti, C ;
Perozzo, V ;
Serra, S .
TETRAHEDRON, 1997, 53 (44) :15029-15040
[2]   A new two step route to 1-hydroxy-9H-3-carbazolecarboxylic acid derivatives from 3-formylindole. Application to the synthesis of mukonine [J].
Brenna, E ;
Fuganti, C ;
Serra, S .
TETRAHEDRON, 1998, 54 (08) :1585-1588
[3]   Synthesis of (+/-)-licarin B and eupomatenoids-1 and -12: A general approach to 2-aryl-7-alkoxy-benzofuranoid neolignans [J].
Engler, TA ;
Chai, WY .
TETRAHEDRON LETTERS, 1996, 37 (39) :6969-6970
[4]   STEREOSPECIFIC LEWIS ACID-PROMOTED REACTIONS OF STYRENYL SYSTEMS WITH 2-ALKOXY-(6-ALKYL)-1,4-BENZOQUINONES - SCOPE, LIMITATIONS, AND SYNTHETIC APPLICATIONS [J].
ENGLER, TA ;
COMBRINK, KD ;
LETAVIC, MA ;
LYNCH, KO ;
RAY, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6567-6587
[5]  
JACKSON AE, 1976, SYNTHESIS-STUTTGART, P685
[6]  
LOVECY A, 1930, J CHEM SOC, V131, P817
[8]  
SHEEN WS, 1994, PHYTOCHEMISTRY, V36, P213, DOI 10.1016/S0031-9422(00)97039-0
[9]   LIGNANS, NEOLIGNANS, AND RELATED-COMPOUNDS [J].
WARD, RS .
NATURAL PRODUCT REPORTS, 1995, 12 (02) :183-205
[10]   ASYMMETRIC-SYNTHESIS OF LIGNANS [J].
WARD, RS .
TETRAHEDRON, 1990, 46 (15) :5029-5041