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

被引:8
作者
GHARBAOUI, T
LEGRAVEREND, M
BISAGNI, E
机构
[1] Laboratoire de synthèse organique, associé au CNRS, Institut Curie-Biologie, 91405 Orsay
关键词
D O I
10.1016/S0040-4039(00)60857-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenylselenenyl bromide permits the efficient synthesis, in two steps, under mild conditions and in good yield of the allylic bromide 8 from 6-chloro-9-(3-methylidene-1-cyclobutyl) purine 4. Depending on the temperature, 9-[(1-hydroxymethyl)-cyclobut-1-ene-3-yl] adenine 1 and 1-(adenin-9-yl)-3-methylidene-but-1-ene-4-ol 2 were then specifically obtained in two steps.
引用
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页码:7141 / 7144
页数:4
相关论文
共 12 条
[1]   ENANTIOSELECTIVE SYNTHESIS OF THE CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN-A BY A CHEMICOENZYMATIC APPROACH [J].
ARITA, M ;
ADACHI, K ;
ITO, Y ;
SAWAI, H ;
OHNO, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4049-4055
[3]  
BORCHARDT RT, 1984, J BIOL CHEM, V259, P4353
[4]  
BOUMCHITA H, 1991, HETEROCYCLES, V32, P867
[5]  
CRANDALL JK, 1983, ORG REACTIONS, V29, P345
[6]   ADENALLENE AND CYTALLENE - ACYCLIC NUCLEOSIDE ANALOGS THAT INHIBIT REPLICATION AND CYTOPATHIC EFFECT OF HUMAN IMMUNODEFICIENCY VIRUS INVITRO [J].
HAYASHI, S ;
PHADTARE, S ;
ZEMLICKA, J ;
MATSUKURA, M ;
MITSUYA, H ;
BRODER, S .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (16) :6127-6131
[7]   NUCLEOSIDES .9. FORMATION OF 2',3'-UNSATURATED PHYRIMIDINE NUCLEOSIDES VIA A NOVEL BETA-ELIMINATION REACTION [J].
HORWITZ, JP ;
CHUA, J ;
DAROOGE, MA ;
NOEL, M ;
KLUNDT, IL .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) :205-&
[8]   1-(2,3-DIDEOXY-BETA-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE - A HIGHLY POTENT AND SELECTIVE ANTI-HIV AGENT [J].
MANSURI, MM ;
STARRETT, JE ;
GHAZZOULI, I ;
HITCHCOCK, MJM ;
STERZYCKI, RZ ;
BRANKOVAN, V ;
LIN, TS ;
AUGUST, EM ;
PRUSOFF, WH ;
SOMMADOSSI, JP ;
MARTIN, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :461-466
[9]   SYNTHESIS OF METHYLENECYCLOBUTYL ADENINE AND CYCLOBUTENYL ADENINE, POTENT ANTIVIRAL CARBOCYCLIC ANALOGS OF OXETANOCIN-A [J].
MARUYAMA, T ;
HANAI, Y ;
SATO, Y .
NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (2-4) :855-864
[10]  
MURUYAMA T, 1990, CHEM PHARM BULL, V38, P2719