Stereospecific synthesis of new 2,3,4,5-piperidinetetracarboxylic acids and 2,3,5-piperidinetricarboxylic acids

被引:17
作者
Arakawa, Y [1 ]
Murakami, T [1 ]
Ozawa, F [1 ]
Arakawa, Y [1 ]
Yoshifuji, S [1 ]
机构
[1] Hokuriku Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201181, Japan
关键词
1,2-dihydropyridine; 2,3,4,5-piperidinetetracarboxylic acid; 2,3,5-piperidinetricarboxylic acid; Diels-Alder adduct; ruthenium tetroxide;
D O I
10.1016/S0040-4020(03)01200-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diels-Alder adducts of 1,2-dihydropyridine with maleic and acrylic acid derivatives were stereospecifically converted by way of RuO4 oxidation into new r-2,c-3,c-4,c-5-piperidinetetracarboxylic acid, r-2,t-3,t-4,c-5-piperidinetetracarboxylic acid, r-2,c-3,c-5-piperidinetricarboxylic acid, and r-2,t-3,c-5-piperidinetricarboxylic acid. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7555 / 7563
页数:9
相关论文
共 10 条
  • [1] Arakawa Y, 1997, CHEM PHARM BULL, V45, P255
  • [2] Stereospecific synthesis of azetidine-cis-2,3-dicarboxylic acid
    Arakawa, Y
    Murakami, T
    Arakawa, Y
    Yoshifuji, S
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (01) : 96 - 97
  • [3] SYNTHESIS OF (+/-)-HOMOGABACULINE AND (+/-)-HOMOSHIKIMIC ACID
    CAMPBELL, MM
    MAHON, MF
    SAINSBURY, M
    SEARLE, PA
    DAVIES, GM
    [J]. TETRAHEDRON LETTERS, 1991, 32 (07) : 951 - 954
  • [4] STEREOSELECTIVE CYCLOADDITION OF N-GLYCOPYRANOSYL 1,2-DIHYDROPYRIDINES WITH METHYL ACRYLATE
    MARAZANO, C
    YANNIC, S
    GENISSON, Y
    MEHMANDOUST, M
    DAS, BC
    [J]. TETRAHEDRON LETTERS, 1990, 31 (14) : 1995 - 1998
  • [5] AMINO-CLAISEN REARRANGEMENTS OF N-VINYLISOQUINUCLIDENES IN NOVEL APPROACHES TO THE SYNTHESIS OF HYDROISOQUINOLINES AND HYDROPHENANTHRIDINES
    MARIANO, PS
    DUNAWAYMARIANO, D
    HUESMANN, PL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (01) : 124 - 133
  • [6] SYNTHESIS OF CHIRAL ISOQUINUCLIDINES AND DETERMINATION OF THEIR ABSOLUTE-CONFIGURATION
    MEHMANDOUST, M
    MARAZANO, C
    SINGH, R
    GILLET, B
    CESARIO, M
    FOURREY, JL
    DAS, BC
    [J]. TETRAHEDRON LETTERS, 1988, 29 (35) : 4423 - 4426
  • [7] DIELS-ALDER REACTIONS BETWEEN TRANS-1-N-ACYLAMINO-1,3-DIENES AND METHYL ACRYLATE - CORRELATION BETWEEN DIENE PHOTOELECTRON IONIZATION-POTENTIALS AND REACTIVITY, STEREOSELECTIVITY, AND REGIOSELECTIVITY
    OVERMAN, LE
    TAYLOR, GF
    HOUK, KN
    DOMELSMITH, LN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (10) : 3182 - 3189
  • [8] DIELS-ALDER ADDUCTS OF "1-BENZENESULFONYLINDOLE-2-ACRYLATES AND 1-(ALKOXYCARBONYL)-1,2-DIHYDROPYRIDINES - INTERMEDIATES FOR SYNTHESIS OF IBOGA ALKALOID ANALOGS
    SUNDBERG, RJ
    BLOOM, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) : 4836 - 4842
  • [9] CYCLOADDITION REACTIONS OF N-METHYL-1,2-DIHYDROPYRIDINE
    WEINSTEIN, B
    LIN, LCC
    FOWLER, FW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) : 1657 - 1661
  • [10] WENDER PA, 1979, TETRAHEDRON LETT, V20, P2485