A short, atom-economical entry to tetrahydroxanthenones

被引：164
作者：
Lesch, B
Bräse, S
机构：
[1] Univ Karlsruhe, Inst Organ Chem, D-76131 Karlsruhe, Germany
[2] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 01期
关键词：
domino reactions; Michael addition; secalonic acids; xanthones;
D O I：
10.1002/anie.200352154
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A reaction that takes to water: The domino Michael addition/aldol condensation of salicylic aldehydes like 1 as the nucleophile and 2-cyclohexen-1-one (2) as the Michael acceptor provides 2,3,4,4a-tetrahydroxanthen-1-ones such as 3 in good yields. DABCO = 1,4-diazabicy-clo[2.2.2]octane.
引用
收藏
页码：115 / 118
页数：4
相关论文
共 51 条
[1]   First-examples of metal and ligand accelerated catalysis of the Baylis-Hillman reaction [J].
Aggarwal, VK ;
Tarver, GJ ;
McCague, R .
CHEMICAL COMMUNICATIONS, 1996, (24) :2713-2714
[2]   Crystal structures of methanol and ethanol solvates of secalonic acid D [J].
Barnes, CL ;
Ubillas, R ;
Tempesta, MS .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1999, 29 (09) :1031-1035
[3]  
BAYLOS AB, 1972, CHEM ABSTR 34174Q, V77
[4]   Oxidative aryl coupling reactions: a biomimetic approach to configurationally unstable or axially chiral biaryl natural products and related bioactive compounds [J].
Bringmann, G ;
Tasler, S .
TETRAHEDRON, 2001, 57 (02) :331-343
[5]   THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].
BRINGMANN, G ;
WALTER, R ;
WEIRICH, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991
[6]  
Bringmann G., 1990, ANGEW CHEM, V102, P1006
[7]   PRODUCTION AND BIOLOGICAL-ACTIVITY OF SECALONIC ACID-D [J].
CIEGLER, A ;
HAYES, AW ;
VESONDER, RF .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1980, 39 (02) :285-287
[8]   Ultrasound in Baylis-Hillman reactions with aliphatic and aromatic aldehydes: scope and limitations [J].
Coelho, F ;
Almeida, WP ;
Veronese, D ;
Mateus, CR ;
Lopes, ECS ;
Rossi, RC ;
Silveira, GPC ;
Pavam, CH .
TETRAHEDRON, 2002, 58 (37) :7437-7447
[9]  
Couladouros E. A., 2002, ANGEW CHEM, V114, P3829
[10]  
Couladouros EA, 2002, ANGEW CHEM INT EDIT, V41, P3677, DOI 10.1002/1521-3773(20021004)41:19<3677::AID-ANIE3677>3.0.CO
123456