Acetogenic isoquinoline alkaloids, part 147.: First total synthesis of the 7,6′-coupled antifungal naphthylisoquinoline alkaloid dioncophylline B

被引:19
作者
Bringmann, G
Günther, C
Peters, EM
Peters, K
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Max Planck Inst Festkorperforsch, D-70506 Stuttgart, Germany
关键词
dioncophylline B; naphthylisoquinoline alkaloids; total synthesis; cross coupling; directed ortho-metalation;
D O I
10.1016/S0040-4020(00)01110-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the antimalarial alkaloid dioncophylline B (2) from Triphyophyllum peltatum (Dioncophyllaceae), and thus the first preparation of a 7,6'-coupled naphthylisoquinoline, is described. Key steps within this synthesis are the ortho-functionalization of the MOM-protected naphthalene and isoquinoline moieties 14 and 7 by directed ortho-metalation, with subsequent stannylation of the naphthalene part and bromination of the isoquinoline portion, and the regioselective intermolecular Stille coupling reaction of these building blocks. The presented synthesis opens the way for the preparation of further 7-coupled compounds of this class of alkaloids. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1253 / 1259
页数:7
相关论文
共 49 条
  • [1] AMATO JS, 1979, SYNTHESIS-STUTTGART, P970
  • [2] Beller M., 1995, ANGEW CHEM, V107, P1992
  • [3] BELLER M, 1995, ANGEW CHEM INT EDIT, V34, P1847
  • [4] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS
    BOYD, MR
    HALLOCK, YF
    MANFREDI, KP
    BLUNT, JW
    MCMAHON, JB
    BUCKHEIT, RW
    BRINGMANN, G
    SCHAFFER, M
    CRAGG, GM
    THOMAS, DW
    JATO, JG
    CARDELLINA, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) : 1740 - 1745
  • [5] ACETOGENIC ISOQUINOLINE ALKALOIDS .17. 1ST TOTAL SYNTHESIS OF (-)-DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND OF SELECTED STEREOISOMERS - COMPLETE (REVISED) STEREOSTRUCTURE
    BRINGMANN, G
    JANSEN, JR
    REUSCHER, H
    RUBENACKER, M
    PETERS, K
    VONSCHNERING, HG
    [J]. TETRAHEDRON LETTERS, 1990, 31 (05) : 643 - 646
  • [6] Acetogenic isoquinoline alkaloids - Part 104 - Molluscicidal activity (Biomphalaria glabrata) of dioncophylline A: Structure-activity investigations
    Bringmann, G
    Holenz, J
    Assi, LA
    Hostettmann, K
    [J]. PLANTA MEDICA, 1998, 64 (05) : 485 - 486
  • [7] BRINGMANN G, 1991, SYNTHESIS-STUTTGART, P825
  • [8] FEEDING DETERRENCY AND GROWTH RETARDING ACTIVITY OF THE NAPHTHYLISOQUINOLINE ALKALOID DIONCOPHYLLINE-A AGAINST SPODOPTERA-LITTORALIS
    BRINGMANN, G
    GRAMATZKI, S
    GRIMM, C
    PROKSCH, P
    [J]. PHYTOCHEMISTRY, 1992, 31 (11) : 3821 - +
  • [9] Dioncophylline A as a growth-retarding agent against the herbivorous insect Spodoptera littoralis: Structure-activity relationships
    Bringmann, G
    Holenz, J
    Wiesen, B
    Nugroho, BW
    Proksch, P
    [J]. JOURNAL OF NATURAL PRODUCTS, 1997, 60 (04): : 342 - 347
  • [10] Ancistroealaines A and B, two new bioactive naphthylisoquinolines, and related naphthoic acids from Ancistrocladus ealaensis
    Bringmann, G
    Hamm, A
    Günther, C
    Michel, M
    Brun, R
    Mudogo, V
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11): : 1465 - 1470