SYNTHESIS OF RACEMIC CARBOACYCLONUCLEOSIDES DERIVED FROM BUTANE-1,4-DIOL AND HEXANE-1,6-DIOL

被引:14
作者
PERBOST, M [1 ]
LUCAS, M [1 ]
CHAVIS, C [1 ]
IMBACH, JL [1 ]
机构
[1] UNIV MONTPELLIER 2,CNRS,CHIM BIOORGAN LAB 488,CASE 008,F-34095 MONTPELLIER 5,FRANCE
来源
NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 08期
关键词
D O I
10.1080/07328319208021191
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of racemic diethyl succinate and dimethyl adipate substituted in their 2 and 3 position respectively by usual heterocyclic bases are described via the Michael addition of nucleobases on diethyl maleate and dimethyl (E)-3-hexene-1, 6-dioate. The Michael adducts are further reduced to afford the corresponding carboacyclonucleosides.
引用
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页码:1489 / 1505
页数:17
相关论文
共 44 条
[1]  
ANDERSEN L, 1988, CHEM SCRIPTA, V28, P307
[2]   A MICHAEL ADDITION WITH 6-CHLOROPURINE [J].
BAKER, BR ;
TANNA, PM .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (08) :2857-&
[3]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF THE ENANTIOMERIC FORMS OF CARBA-5-IODO-2'-DEOXYURIDINE AND CARBA-(E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE [J].
BALZARINI, J ;
BAUMGARTNER, H ;
BODENTEICH, M ;
DECLERCQ, E ;
GRIENGL, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) :1861-1865
[4]  
Balzarini J., 1990, PHARM CHEM LIBRARY S, V14, P175
[5]   SNCL4 VERSUS TICL4-MEDIATED COUPLING BETWEEN N-6-BENZOYLADENINE AND PERBENZOYLATED 2-DEOXYPYRANOSE - APPLICATION TO THE SYNTHESIS OF CERTAIN HOMOCHIRAL ACYCLONUCLEOSIDES AND CARBOACYCLONUCLEOSIDES [J].
BAUD, MV ;
CHAVIS, C ;
LUCAS, M ;
IMBACH, JL .
TETRAHEDRON, 1991, 47 (48) :9993-10002
[6]   FLUORO CARBOCYCLIC NUCLEOSIDES - SYNTHESIS AND ANTIVIRAL ACTIVITY OF 2'-FLUORO AND 6'-FLUORO CARBOCYCLIC PYRIMIDINE NUCLEOSIDES INCLUDING CARBOCYCLIC 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)-5-METHYLURACIL AND CARBOCYCLIC 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)-5-IODOURACIL [J].
BORTHWICK, AD ;
EVANS, DN ;
KIRK, BE ;
BIGGADIKE, K ;
EXALL, AM ;
YOUDS, P ;
ROBERTS, SM ;
KNIGHT, DJ ;
COATES, JAV .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :179-186
[7]  
BUEHLER CA, 1970, SURVEY ORGANIC SYNTH, P468
[9]   CHEMISTRY AND ANTIVIRAL ACTIVITIES OF ACYCLONUCLEOSIDES [J].
CHU, CK ;
CUTLER, SJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (02) :289-319
[10]   SYNTHESIS OF COMPOUNDS ACTIVE AGAINST HIV .2. PREPARATION OF SOME 2',3'-DIDEOXY-6'-FLUOROCARBOCYCLIC NUCLEOSIDES [J].
COE, DM ;
MYERS, PL ;
PARRY, DM ;
ROBERTS, SM ;
STORER, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (02) :151-153