Diastereoselective and enantioselective synthesis of 4′-aza analogues of 2′,3′-dideoxynucleosides

被引:41
作者
Chiacchio, U
Rescifina, A
Corsaro, A
Pistarà, V
Romeo, G
Romeo, R
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[2] Univ Messina, Dipartimento Farmaco Chim, I-98100 Messina, Italy
关键词
D O I
10.1016/S0957-4166(00)00160-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A diastereo- and enantioselective synthesis of 4'-aza analogues of 2',3'-dideoxynucleosides has been designed by the strategy of the 1,3-dipolar cycloaddition reaction of a Vasella-type nitrone. The reaction leads to (1'R)- and (1'S)-4'-aza analogues of 2',3'-dideoxythimidine and fluorouridine, in enantiomerically pure forms. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2045 / 2048
页数:4
相关论文
共 25 条
[1]   Heterocyclic nucleoside analogues by cycloaddition reactions of 1-vinylthymine with 1,3-dipoles [J].
Adams, DR ;
Boyd, ASF ;
Ferguson, R ;
Grierson, DS ;
Monneret, C .
NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (06) :1053-1075
[2]  
BONNET PA, 1995, J CURR OPIN ONCOLOGY, V8, P525
[3]   Stereoselective synthesis of 2′-amino-2′,3′-dideoxynucleosides by nitrone 1,3-dipolar cycloaddition:: A new efficient entry toward d4T and its 2-methyl analogue [J].
Chiacchio, U ;
Rescifina, A ;
Iannazzo, D ;
Romeo, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :28-36
[4]   Homochiral α-D- and β-D-isoxazolidinylthymidines via 1,3-dipolar cycloaddition [J].
Chiacchio, U ;
Corsaro, A ;
Gumina, G ;
Rescifina, A ;
Iannazzo, D ;
Piperno, A ;
Romeo, G ;
Romeo, R .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9321-9327
[5]  
Collins A.N., 1992, CHIRALITY IND
[6]   TOWARD IMPROVED ANTI-HIV CHEMOTHERAPY - THERAPEUTIC STRATEGIES FOR INTERVENTION WITH HIV-INFECTIONS [J].
DECLERCQ, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2491-2517
[7]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[8]   Synthesis of dihydroisoxazole nucleoside and nucleotide analogs [J].
Gi, HJ ;
Xiang, YJ ;
Schinazi, RF ;
Zhao, K .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :88-92
[9]  
HUANG BG, 1993, SYNTHESIS-STUTTGART, P769
[10]   L-BETA-(2S,4S)-DIOXOLANYL AND L-ALPHA-(2S,4R)-DIOXOLANYL NUCLEOSIDES AS POTENTIAL ANTI-HIV AGENTS - ASYMMETRIC-SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
KIM, HO ;
SCHINAZI, RF ;
SHANMUGANATHAN, K ;
JEONG, LS ;
BEACH, JW ;
NAMPALLI, S ;
CANNON, DL ;
CHU, CK .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (05) :519-528