SYNTHESIS OF NEW CARBOCYCLIC OXETANOCIN ANALOGS

被引:17
作者
GHARBAOUI, T
LEGRAVEREND, M
LUDWIG, O
BISAGNI, E
AUBERTIN, AM
CHERTANOVA, L
机构
[1] CTR UNIV ORSAY,INST CURIE,BIOL SECT,SYNTH ORGAN LAB,CNRS,URA 1387,F-91405 ORSAY,FRANCE
[2] UNIV STRASBOURG 1,INSERM,U74,F-67000 STRASBOURG,FRANCE
[3] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/0040-4020(94)01031-T
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carbocyclic oxetanocin analogues containing 3-fluoro or 3-hydroxy cyclobutyl moieties and different natural bases, have been prepared from the olefinic precursors either by direct fluoro-iodination (AgF-I-2) or by DAST fluorination of the bromhydrin. The latter allowed the synthesis of the corresponding phosphonate derivatives as well.
引用
收藏
页码:1641 / 1652
页数:12
相关论文
共 23 条
[1]  
[Anonymous], 1986, SHELXS86 PROGRAM SOL
[2]   2'-DEOXY-2'-FLUORO-ARA-ARISTEROMYCIN, A NEW ANTI-HERPES AGENT - THE 1ST DIRECT INTRODUCTION OF A 2'-FLUORO SUBSTITUENT INTO A CARBOCYCLIC NUCLEOSIDE [J].
BIGGADIKE, K ;
BORTHWICK, AD ;
EXALL, AM ;
KIRK, BE ;
WARD, RA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (13) :898-900
[3]  
BOUMCHITA H, 1991, HETEROCYCLES, V32, P867
[4]   BROMOHYDRINS OF METHYLENECYCLOBUTANE [J].
ERICKSON, KL ;
KIM, K .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (19) :2915-&
[5]   AN EFFICIENT SYNTHESIS OF 9-[(1-HYDROXYMETHYL)-CYCLOBUT-1-ENE-3-YL] ADENINE AND 1-(ADENIN-9-YL)-3-METHYLIDENE-BUT-1-ENE-4-OL VIA REGIOSPECIFIC ADDITION OF PHENYL SELENENYL BROMIDE TO THE ALKENE PRECURSOR [J].
GHARBAOUI, T ;
LEGRAVEREND, M ;
BISAGNI, E .
TETRAHEDRON LETTERS, 1992, 33 (47) :7141-7144
[6]   CYCLOBUT-A AND CYCLOBUT-G, CARBOCYCLIC OXETANOCIN ANALOGS THAT INHIBIT THE REPLICATION OF HUMAN-IMMUNODEFICIENCY-VIRUS IN T-CELLS AND MONOCYTES AND MACROPHAGES INVITRO [J].
HAYASHI, S ;
NORBECK, DW ;
ROSENBROOK, W ;
FINE, RL ;
MATSUKURA, M ;
PLATTNER, JJ ;
BRODER, S ;
MITSUYA, H .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1990, 34 (02) :287-294
[7]   SYNTHESIS OF SQ-32,829, A NEW NUCLEOSIDE ANTIVIRAL AGENT [J].
JACOBS, GA ;
TINO, JA ;
ZAHLER, R .
TETRAHEDRON LETTERS, 1989, 30 (50) :6955-6958
[8]   4'-SUBSTITUTED NUCLEOSIDES .2. SYNTHESIS OF NUCLEOSIDE ANTIBIOTIC NUCLEOCIDIN [J].
JENKINS, ID ;
VERHEYDEN, JPH ;
MOFFATT, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (11) :3346-3357
[9]   NOVEL CARBOCYCLIC NUCLEOSIDES RELATED TO OXETANOCIN [J].
JOHNSON, CR ;
DEJONG, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :594-599
[10]   EFFICIENT TOTAL SYNTHESIS OF RACEMIC AND OPTICALLY-ACTIVE CYCLOBUT-A AND SIMPLE ANALOGS [J].
JUNG, ME ;
SLEDESKI, AW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (07) :589-591