Convenient synthesis of linear pyrano[3,2-g]-,[2,3-g]- and angular pyrano[3,2-f]coumarins from 4-[(1,1-dimethyl-2-propynyl)oxy]phenol

被引:16
作者
Baldoumi, V. [1 ]
Gautam, D. R. [1 ]
Litinas, K. E. [1 ]
Nicolaides, D. N. [1 ]
机构
[1] Aristotle Univ Thessaloniki, Organ Chem Lab, Thessaloniki 54124, Greece
关键词
pyranocoumarins; xanthyletin; phenols; DMAD; Ph3P; Wittig reaction; delta-lactonization; dealkoxycarbonylation;
D O I
10.1016/j.tet.2006.06.032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An easy preparation of new 4-alkoxycarbonyl angular and linear pyranocoumarins starting from 4-[(1,1-dimethyl-2-propynyl)oxy]phenol and their transformation to the known coumarins xanthyletin, 8,8-dimethylpyrano[3,2 f]chromen-3(8H)-one and 7,7-dimethylpyrano[2,3-g]chromen-2(7H)-one is described. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8016 / 8020
页数:5
相关论文
共 22 条
[1]   SYNTHESIS OF LINEAR 3-PHENYLPYRANOCOUMARINS - SYNTHESIS OF ROBUSTIN, ROBUSTIC ACID, AND THEIR METHYL ETHERS [J].
AHLUWALIA, VK ;
PRAKASH, C ;
JOLLY, RS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1697-1702
[2]  
Bestmann H. J., 1969, TETRAHEDRON LETT, V10, P2101
[3]   STUDIES OF CHROMENES .9. SYNTHESES OF CHROMENEQUINONES [J].
BROWN, PE ;
LEWIS, RA ;
WARING, MA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :2979-2988
[4]   TORTUOSIDE, A NEW NATURAL COUMARIN GLUCOSIDE FROM SESELI-TORTUOSUM [J].
CECCHERELLI, P ;
CURINI, M ;
MARCOTULLIO, MC ;
MADRUZZA, G ;
MENGHINI, A .
JOURNAL OF NATURAL PRODUCTS, 1989, 52 (04) :888-890
[5]   Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities [J].
Fylaktakidou, KC ;
Hadjipavlou-Litina, DJ ;
Litinas, KE ;
Nicolaides, DN .
CURRENT PHARMACEUTICAL DESIGN, 2004, 10 (30) :3813-3833
[6]   Reactions of 4-methylchromene-2,7,8-trione with phosphonium ylides. Synthesis and evaluation of fused 1,3-dioxolocoumarins as antioxidants and antiinflammatories [J].
Fylaktakidou, KC ;
Gautam, DR ;
Hadjipavlou-Litina, DJ ;
Kontogiorgis, CA ;
Litinas, KE ;
Nicolaides, DN .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :3073-3079
[7]  
Majumdar KC, 1996, J CHEM RES-S, P462
[8]   Efficient syntheses of 6-prenylcoumarins and linear pyranocoumarins:: Total synthesis of suberosin, toddaculin, O-methylapigravin (O-methylbrosiperin), O-methylbalsamiferone, dihydroxanthyletin, xanthyletin and luvangetin [J].
Mali, RS ;
Joshi, PP ;
Sandhu, PK ;
Manekar-Tilve, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (03) :371-376
[9]   CONVENIENT 2-STEP SYNTHESES OF SESELIN AND ANGELICIN DERIVATIVES [J].
MALI, RS ;
PANDHARE, NA ;
SINDKHEDKAR, MD .
TETRAHEDRON LETTERS, 1995, 36 (39) :7109-7110
[10]  
Murray R D H, 1982, NATURAL COUMARINS