A NEW APPROACH TO THE SYNTHESIS OF LAVENDAMYCIN ANALOGS

被引:27
作者
ROCCA, P [1 ]
MARSAIS, F [1 ]
GODARD, A [1 ]
QUEGUINER, G [1 ]
机构
[1] INSA,CHIM ORGAN FINE & HETEROCYCL LAB,CNRS,BP 08,F-76131 MONT ST AIGNAN,FRANCE
关键词
ALKALOID; BETA-CARBOLINE; CROSS-COUPLING; HALOPYRIDINES; METALATION;
D O I
10.1016/S0040-4039(00)60486-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-steps approach to the lavendamycin skeleton from benzene, pyridine and quinoline blocks is described. It is based on a new synthetic methodology for the preparation of alpha-substituted beta-carbolines which involves such reactions as Directed Ortho Metalation and Heteroring Cross-Coupling.
引用
收藏
页码:2937 / 2940
页数:4
相关论文
共 25 条
  • [1] BALITZ DM, 1982, ANTIBIOTICS, V25, P261
  • [2] BOGER DL, 1984, TETRAHEDRON LETT, V25, P3175
  • [3] STRUCTURE DETERMINATION OF LAVENDAMYCIN - A NEW ANTI-TUMOR ANTIBIOTIC FROM STREPTOMYCES-LAVENDULAE
    DOYLE, TW
    BALITZ, DM
    GRULICH, RE
    NETTLETON, DE
    GOULD, SJ
    TANN, CH
    MOEWS, AE
    [J]. TETRAHEDRON LETTERS, 1981, 22 (46) : 4595 - 4598
  • [4] Fox B.A., 1973, ORG SYNTH, V5, P346
  • [5] CONNECTIONS TO THE DIRECTED ORTHO METALATION STRATEGY - PD(0)-CATALYZED CROSS COUPLING OF ARYL BORONIC ACIDS WITH ARYL TRIFLATES
    FU, JM
    SNIECKUS, V
    [J]. TETRAHEDRON LETTERS, 1990, 31 (12) : 1665 - 1668
  • [6] CONVERGENT SYNTHESIS OF THE STREPTONIGRIN ALKALOID SKELETON - DIRECTED ORTHOMETALATION CONNECTION TO ARYL-ARYL CROSS-COUPLING
    GODARD, A
    ROVERA, JC
    MARSAIS, F
    PLE, N
    QUEGUINER, G
    [J]. TETRAHEDRON, 1992, 48 (20) : 4123 - 4134
  • [7] GRONOWITZ S, 1984, CHEM SCRIPTA, V24, P5
  • [8] Gschwend H.W., 1976, ORG REACT NY, V26, P1
  • [9] SYNTHETIC APPROACH TO THE ANTI-TUMOR ANTIBIOTIC LAVENDAMYCIN - A SYNTHESIS OF DEMETHYLLAVENDAMYCIN METHYL-ESTER
    HIBINO, S
    OKAZAKI, M
    SATO, K
    MORITA, I
    ICHIKAWA, M
    [J]. HETEROCYCLES, 1983, 20 (10) : 1957 - 1958
  • [10] ISHIKURA M, 1985, HETEROCYCLES, V23, P2375