Palladium-catalyzed intramolecular δ-lactam formation of aryl halides and amide-enolates:: Syntheses of cherylline and latifine

被引:76
作者
Honda, T [1 ]
Namiki, H [1 ]
Satoh, F [1 ]
机构
[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan
关键词
D O I
10.1021/ol0155337
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Palladium-catalyzed intramolecular carbon-carbon bond formation of aryl halides and amide enolates gave 4-arylisoquinoline derivatives in good yields, which were further converted into the isoquinoline alkaloids cherylline and latifine.
引用
收藏
页码:631 / 633
页数:3
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共 21 条
  • [1] Radical cyclizations.: A convergent total synthesis of (±)-γ-lycorane
    Cossy, J
    Tresnard, L
    Pardo, DG
    [J]. TETRAHEDRON LETTERS, 1999, 40 (06) : 1125 - 1128
  • [2] STUDIES ON DOPAMINE AGONIST PROPERTIES OF 8-AMINO-2-METHYL-4-(3,4-DIHYDROXYPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE, A DERIVATIVE OF NOMIFENSINE
    COSTALL, B
    NAYLOR, RJ
    [J]. JOURNAL OF PHARMACY AND PHARMACOLOGY, 1978, 30 (08) : 514 - 516
  • [3] Base-induced cyclization of trimethoxy-o-aroyldiphenylphosphoryl methylbenzamide: A formal synthesis of (+/-)cherylline and (+/-)cherylline dimethylether
    Couture, A
    Deniau, E
    Woisel, P
    Grandclaudon, P
    Carpentier, JF
    [J]. TETRAHEDRON LETTERS, 1996, 37 (21) : 3697 - 3700
  • [4] Total syntheses of (±)-cherylline and (±)-latifine
    Couture, A
    Deniau, E
    Lebrun, S
    Grandclaudon, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (07): : 789 - 794
  • [5] ALPHA'-SILYLATED TERTIARY BENZAMIDES AS DUAL ORTHO-CARBANION AND ALPHA'-CARBANION SYNTHONS - CARBODESILYLATIVE ROUTES TO ISOQUINOLINE AND DIBENZOQUINOLIZIDINE DERIVATIVES
    CUEVAS, JC
    SNIECKUS, V
    [J]. TETRAHEDRON LETTERS, 1989, 30 (43) : 5837 - 5840
  • [6] A convergent approach to huperzine A and analogues
    Foricher, Y
    Mann, J
    [J]. TETRAHEDRON LETTERS, 2000, 41 (12) : 2007 - 2009
  • [7] Highly active and selective catalysts for the formation of α-aryl ketones
    Fox, JM
    Huang, XH
    Chieffi, A
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) : 1360 - 1370
  • [8] ENANTIOSELECTIVE SYNTHESIS OF INDOLIZIDINE ALKALOIDS - FORMAL SYNTHESIS OF ((-))-SWAINSONINE AND OF (+)-PUMILIOTOXIN 251D
    HONDA, T
    HOSHI, M
    KANAI, K
    TSUBUKI, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2091 - 2101
  • [9] DOPAMINE AGONIST PROPERTIES OF N-ALKYL-4-(3,4-DIHYDROXYPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINES
    JACOB, JN
    NICHOLS, DE
    KOHLI, JD
    GLOCK, D
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (08) : 1013 - 1015
  • [10] A FACILE TOTAL SYNTHESIS OF (+/-)-CHERYLLINE VIA AN AZIRIDINIUM INTERMEDIATE
    KAMETANI, T
    HIGASHIYAMA, K
    HONDA, T
    OTOMASU, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (12): : 2935 - 2937