Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

被引:36
作者
Amblard, F
Nolan, SP
Schinazi, RF
Agrofoglio, LA
机构
[1] CNRS, UMR 6005, ICOA, F-45067 Orleans 2, France
[2] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
[3] Emory Univ, Vet Affairs Med Ctr, Atlanta, GA 30033 USA
[4] Emory Univ, Biochem Pharmacol Lab, Atlanta, GA 30033 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tet.2004.11.019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:537 / 544
页数:8
相关论文
共 54 条
  • [11] HIGHLY SELECTIVE CROSS-METATHESIS OF TERMINAL OLEFINS
    CROWE, WE
    ZHANG, ZJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) : 10998 - 10999
  • [12] BROAD-SPECTRUM ANTI-DNA VIRUS AND ANTIRETROVIRUS ACTIVITY OF PHOSPHONYLMETHOXYALKYLPURINES AND PHOSPHONYLMETHOXYALKYLPYRIMIDINES
    DECLERCQ, E
    [J]. BIOCHEMICAL PHARMACOLOGY, 1991, 42 (05) : 963 - 972
  • [13] DECLERCQ E, 1990, DRUG EXP CLIN RES, V16, P319
  • [14] EFFICACY OF (S)-1-(3-HYDROXY-2-PHOSPHONYLMETHOXYPROPYL)CYTOSINE IN VARIOUS MODELS OF HERPES-SIMPLEX VIRUS-INFECTION IN MICE
    DECLERCQ, E
    HOLY, A
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1991, 35 (04) : 701 - 706
  • [15] A NOVEL SELECTIVE BROAD-SPECTRUM ANTI-DNA VIRUS AGENT
    DECLERCQ, E
    HOLY, A
    ROSENBERG, I
    SAKUMA, T
    BALZARINI, J
    MAUDGAL, PC
    [J]. NATURE, 1986, 323 (6087) : 464 - 467
  • [16] DECLERCQ E, 1990, TRENDS DRUG RES, P133
  • [17] SELECTIVITY OF ACTION OF AN ANTI-HERPETIC AGENT, 9-(2-HYDROXYETHOXYMETHYL)GUANINE
    ELION, GB
    FURMAN, PA
    FYFE, JA
    DEMIRANDA, P
    BEAUCHAMP, L
    SCHAEFFER, HJ
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1977, 74 (12) : 5716 - 5720
  • [18] INHIBITION OF HERPES-SIMPLEX VIRUS-INDUCED DNA-POLYMERASE ACTIVITY AND VIRAL-DNA REPLICATION BY 9-(2-HYDROXYETHOXYMETHYL)GUANINE AND ITS TRIPHOSPHATE
    FURMAN, PA
    STCLAIR, MH
    FYFE, JA
    RIDEOUT, JL
    KELLER, PM
    ELION, GB
    [J]. JOURNAL OF VIROLOGY, 1979, 32 (01) : 72 - 77
  • [19] Fürstner A, 2000, ANGEW CHEM INT EDIT, V39, P3012
  • [20] Palladium(0)-catalysed allylation of uracils and thiouracils. Influence of the solvent on the regioselectivity of the allylation
    Goux, C
    Sigismondi, S
    Sinou, D
    Perez, M
    MorenoManas, M
    Pleixats, R
    Villarroya, M
    [J]. TETRAHEDRON, 1996, 52 (28) : 9521 - 9534