SYNTHESIS OF THE BENZO[B]CARBAZOLOQUINONE WITH THE STRUCTURE PROPOSED FOR PREKINAMYCIN

被引:31
作者
ECHAVARREN, AM [1 ]
TAMAYO, N [1 ]
PAREDES, MC [1 ]
机构
[1] CSIC,INST QUIM ORGAN,E-28006 MADRID,SPAIN
关键词
D O I
10.1016/S0040-4039(00)60664-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the N-cyano benzo[b]carbazolequinone with the structure proposed for prekinamycin has been achieved by palladium and copper catalyzed coupling of a 2-bromonaphthoquinone with an arylstannane followed by ring closure, N-cyanation, and demethylation. Unexpectedly, the ring closure reaction gave also a regioisomer by an unprecedented rearrangement reaction.
引用
收藏
页码:4713 / 4716
页数:4
相关论文
共 23 条
  • [1] JADOMYCIN, A NOVEL 8H-BENZ[B]OXAZOLO[3,2-F]PHENANTHRIDINE ANTIBIOTIC FROM STREPTOMYCES-VENEZUELAE ISP5230
    AYER, SW
    MCINNES, AG
    THIBAULT, P
    WALTER, JA
    DOULL, JL
    PARNELL, T
    VINING, LC
    [J]. TETRAHEDRON LETTERS, 1991, 32 (44) : 6301 - 6304
  • [2] NEW TOTAL SYNTHESIS OF BIKAVERIN
    BEKAERT, A
    ANDRIEUX, J
    PLAT, M
    [J]. TETRAHEDRON LETTERS, 1992, 33 (20) : 2805 - 2806
  • [3] The bromination of 1 5-dihydroxy- and 1 5-diacetoxy-naphthalene, 5-methoxy1-naphthol, and 1 5-dimethoxynaphthalene
    Carter, AH
    Race, E
    Rowe, FM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1942, : 236 - 239
  • [4] NEW PRODUCTS RELATED TO KINAMYCIN FROM STREPTOMYCES-MURAYAMAENSIS .1. TAXONOMY, PRODUCTION, ISOLATION AND BIOLOGICAL PROPERTIES
    CONE, MC
    SEATON, PJ
    HALLEY, KA
    GOULD, SJ
    [J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (02) : 179 - 188
  • [5] KINAFLUORENONE, A BENZO[B]FLUORENONE ISOLATED FROM THE KINAMYCIN PRODUCER STREPTOMYCES-MURAYAMAENSIS
    CONE, MC
    MELVILLE, CR
    GORE, MP
    GOULD, SJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) : 1058 - 1061
  • [6] N-CYANOINDOLES AND N-CYANOINDOLE-4,7-DIONES - CONSTRUCTION OF A BC RING SYNTHON FOR THE KINAMYCINS
    DMITRIENKO, GI
    NIELSEN, KE
    STEINGART, C
    MING, NS
    WILLSON, JM
    WEERATUNGA, G
    [J]. TETRAHEDRON LETTERS, 1990, 31 (26) : 3681 - 3684
  • [7] FENDRICH G, Patent No. 304400
  • [8] SYNTHESIS OF PUTATIVE INTERMEDIATES IN THE BIOSYNTHESIS OF THE KINAMYCIN ANTIBIOTICS - TOTAL SYNTHESIS OF PHENANTHROVIRIDIN AGLYCON AND RELATED-COMPOUNDS
    GORE, MP
    GOULD, SJ
    WELLER, DD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2774 - 2783
  • [9] GORE MP, 1990, J ORG CHEM, V56, P2289
  • [10] SYNTHESIS OF BROMONAPHTHOQUINONES FROM 1,5-DIMETHOXYNAPHTHALENE
    HANNAN, RL
    BARBER, RB
    RAPOPORT, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) : 2153 - 2158