Stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[c]furan core

被引:34
作者
Ewing, DF [1 ]
Fahmi, NE [1 ]
Len, C [1 ]
Mackenzie, G [1 ]
Pranzo, A [1 ]
机构
[1] Univ Hull, Dept Chem, Hull HU6 7RX, N Humberside, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 21期
关键词
D O I
10.1039/b006417n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new efficient route is described to uracil, thymidine and cytosine derivatives of 1,3-dihydrobenzo[c]furan which are aromatic analogues of the well known antiviral 2',3'-dideoxy-2',3'-didehydronucleosides. These systems contain two chiral centres (corresponding to alpha/beta and D/L centres in a furanose sugar) and a route involving application of the Sharpless asymmetric oxidation methodology allowed access to each of the four stereoisomers of the uracil derivative in enantiomerically pure form.
引用
收藏
页码:3561 / 3565
页数:5
相关论文
共 21 条
[1]  
BALZARINI J, 1987, MOL PHARMACOL, V32, P162
[2]   Enantiomeric syntheses of conformationally restricted D- and L-2′,3′-dideoxy-2′,3′-endo-methylene nucleosides from carbohydrate chiral templates [J].
Chun, BK ;
Olgen, S ;
Hong, JH ;
Newton, MG ;
Chu, CK .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :685-693
[3]  
CRIMMINS MT, 1996, J ORG CHEM, V61, P1236
[4]  
DECLERCQ E, 1990, DESIGN ANTIAIDS DRUG, V14
[5]   4-(1,2,4-TRIAZOL-1-YL) AND 4-(3-NITRO-1,2,4-TRIAZOL-1-YL)-1-(BETA-D-2,3,5-TRI-O-ACETYLARABINOFURANOSYL)PYRIMIDIN-2(1H)-ONES - VALUABLE INTERMEDIATES IN THE SYNTHESIS OF DERIVATIVES OF "1-(BETA-D-ARABINOFURANOSYL)CYTOSINE (ARA-C) [J].
DIVAKAR, KJ ;
REESE, CB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (05) :1171-1176
[6]   Nucleoside analogues with a novel glycone based on the benzo[c]furan core [J].
Ewing, DF ;
Fahmi, NE ;
Len, C ;
Mackenzie, G ;
Ronco, G ;
Villa, P ;
Shaw, G .
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (11-12) :2613-2630
[7]   (1S,2R)-[(benzyloxy)methyl]cyclopent-3-enol. A versatile synthon for the preparation of 4',1'a-methano- and 1',1'a-methanocarbocyclic nucleosides [J].
Ezzitouni, A ;
Russ, P ;
Marquez, VE .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4870-4873
[8]   AIDS-DRIVEN NUCLEOSIDE CHEMISTRY [J].
HURYN, DM ;
OKABE, M .
CHEMICAL REVIEWS, 1992, 92 (08) :1745-1768
[9]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[10]  
KRAYEVSKY AA, 1993, NUCL NUCL ANTITUMOR