Synthetic approach to preparation of indole derivatives fused with a bicyclo[3.3.1]nonane framework

被引:8
作者
Baranova, T. Yu. [1 ]
Zefirova, O. N. [1 ]
Averina, N. V. [1 ]
Boyarskikh, V. V. [1 ]
Borisova, G. S. [1 ]
Zyk, N. V. [1 ]
Zefirov, N. S. [1 ]
机构
[1] Moscow MV Lomonosov State Univ, Moscow 119992, Russia
基金
俄罗斯基础研究基金会;
关键词
D O I
10.1134/S1070428007080192
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic procedures for N-(2-methoxy-6,7,8,9,10,11-hexahydro-5H-6,10-methanocycloocta[b]-indol-9-yl)acetamide were investigated. The desired product was obtained from the mono ethylene ketal of bicyclo[3.3.1]nonane-2,6-dione in a six-stage procedure involving as the key point the formation of an indole fragment on the bicyclo[3.3.1]nonane framework by Fischer reaction.
引用
收藏
页码:1196 / 1201
页数:6
相关论文
共 11 条
  • [1] FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .11. SYNTHESIS OF 2-AZABICYCLO[3.3.1]NONAN-3,7-DIONES AND THEIR FISCHER INDOLIZATION
    AMAT, M
    SANFELIU, E
    BONJOCH, J
    BOSCH, J
    [J]. TETRAHEDRON LETTERS, 1989, 30 (29) : 3841 - 3844
  • [2] New asymmetric routes to ajmaline and suaveoline indole alkaloids
    Bailey, PD
    Morgan, KM
    Smith, DI
    Vernon, JM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21): : 3566 - 3577
  • [3] The total synthesis of (-)-suaveoline
    Bailey, PD
    Morgan, KM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21): : 3578 - 3583
  • [4] Synthesis and chiroptical properties of methanocycloocta[b] indoles
    Butkus, E
    Berg, U
    Malinauskiene, J
    Sandström, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) : 1353 - 1358
  • [5] GENERAL-APPROACH FOR THE SYNTHESIS OF AJMALINE-RELATED ALKALOIDS - ENANTIOSPECIFIC TOTAL SYNTHESIS OF (-)-SUAVEOLINE, (-)-RAUMACLINE, AND (-)-NB-METHYLRAUMACLINE
    FU, XY
    COOK, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) : 661 - 672
  • [6] 5,9-METHANOBENZOANNULENAMINES .1. IMPROVED SYNTHESIS OF 11-AMINO-5,9-METHANOBENZO[8]ANNULENES
    GILBERT, IM
    HEWETT, CL
    RAE, DR
    REDPATH, J
    SAVAGE, DS
    SLEIGH, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (02): : 133 - 139
  • [7] KADZYAUSKAS PP, 1979, KHIM GETEROTSIKL+, P315
  • [8] ASTERANES .6. SYNTHESIS OF TRICYCLO[3,3,1,02,8]NONANE DERIVATIVES
    KLUSACEK, H
    MUSSO, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (10): : 3066 - +
  • [9] KOST AN, 1971, KHIM GETEROTSIKL+, P512
  • [10] KOST AN, 1967, KHIM GETEROTSIKL+, P16