An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition

被引：171
作者：
Cravotto, G
Nano, GM
Palmisano, G
Tagliapietra, S
机构：
[1] Dipartimento Sci Chim Fis & Matemat, I-22100 Como, Italy
[2] Dipartimento Sci & Tecnol Farmaco, I-10125 Turin, Italy
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 05期
关键词：
D O I：
10.1016/S0957-4166(01)00124-0
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
We have developed a general, two-step protocol for the synthesis of chiral non-racemic coumarin anticoagulants (e.g. warfarin. coumachlor and acenocoumarol). This approach features a one-pot three-component tandem Knoevenagel-hetero-Diels-Alder reaction between in situ generated 3-arylidene-2,4-chromanediones and iso-propenyl ether derived from (-)-menthol. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：707 / 709
页数：3
相关论文
共 34 条
[1]  
Annunziata R, 1997, MAGN RESON CHEM, V35, P721, DOI 10.1002/(SICI)1097-458X(199711)35:11<721::AID-OMR161>3.0.CO
[2]  
2-I
[3]   THE CHEMISTRY OF COUMARIN DERIVATIVES .2. REACTION OF 4-HYDROXYCOUMARIN WITH ALPHA,BETA-UNSATURATED ALDEHYDES [J].
APPENDINO, G ;
CRAVOTTO, G ;
TAGLIAPIETRA, S ;
NANO, GM ;
PALMISANO, G .
HELVETICA CHIMICA ACTA, 1990, 73 (07) :1865-1878
[4]   THE CHEMISTRY OF COUMARIN DERIVATIVES .6. DIELS-ALDER TRAPPING OF 3-METHYLENE-2,4-CHROMANDIONE - A NEW ENTRY TO SUBSTITUTED PYRANO[3,2-C]COUMARINS [J].
APPENDINO, G ;
CRAVOTTO, G ;
TOMA, L ;
ANNUNZIATA, R ;
PALMISANO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5556-5564
[5]   FOAM FLOTATION ENRICHMENT OF ENANTIOMERS [J].
ARMSTRONG, DW ;
ZHOU, EY ;
CHEN, SS ;
LE, K ;
TANG, YB .
ANALYTICAL CHEMISTRY, 1994, 66 (23) :4278-4282
[6]   ENANTIOSELECTIVE STRUCTURE-PHARMACOKINETIC RELATIONSHIPS OF RING SUBSTITUTED WARFARIN ANALOGS IN THE RAT [J].
BAARS, LGM ;
SCHEPERS, MT ;
HERMANS, JJR ;
DAHLMANS, HJJ ;
THIJSSEN, HHW .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1990, 42 (12) :861-866
[7]   2-PHENYLSULFONYL 1,3-DIENES IN ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL ENAMINES AND ENOL ETHERS [J].
BACKVALL, JE ;
RISE, F .
TETRAHEDRON LETTERS, 1989, 30 (39) :5347-5348
[8]   SYNTHESIS AND MECHANISTIC STUDY OF NOVEL PI-BASIC CHIRAL STATIONARY PHASES DERIVED FROM TYROSINE [J].
BARGMANNLEYDER, N ;
TAMBUTE, A ;
BEGOS, A ;
CAUDE, M .
CHROMATOGRAPHIA, 1993, 37 (7-8) :433-443
[9]  
Boger D. L., 1987, ORGANIC CHEM SERIES, V47, P167
[10]  
CHOUDHURY A, 1989, TETRAHEDRON LETT, V30, P4291
1234