Synthesis of the marine dibromooxoindoline convolutamydine C

被引:48
作者
Miah, S
Moody, CJ
Richards, IC
Slawin, AMZ
机构
[1] LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
[2] AGREVO LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 16期
关键词
D O I
10.1039/a700683g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of the marine 4,6-dibromo-3-hydroxyoxoindoline convolutamydine C3 is described. The key steps are the rhodium(II) perfluorobutyramide catalysed cyclisation of diazoamide 17 to give the oxoindoline 18, and the subsequent high yielding one-pot hydrolysis-decarboxylation-oxidation of 19 to 20. X-Ray crystal structures have been determined for the diazoamides 10 and 17 and for the oxoindolines 11 and 13.
引用
收藏
页码:2405 / 2412
页数:8
相关论文
共 41 条
  • [21] APPLICATION OF INTRAMOLECULAR CARBENOID REACTIONS IN ORGANIC-SYNTHESIS
    PADWA, A
    KRUMPE, KE
    [J]. TETRAHEDRON, 1992, 48 (26) : 5385 - 5453
  • [22] Cascade processes of metallo carbenoids
    Padwa, A
    Weingarten, MD
    [J]. CHEMICAL REVIEWS, 1996, 96 (01) : 223 - 269
  • [23] PADWA A, 1994, ANGEW CHEM INT EDIT, V33, P1797, DOI 10.1002/anie.199417971
  • [24] QUALLICH GJ, 1993, TETRAHEDRON LETT, P51
  • [25] RIGBY JH, 1995, SYNLETT, P547
  • [26] TOTAL SYNTHESIS OF (+)-FURANOMYCIN AND STEREOISOMERS
    SEMPLE, JE
    WANG, PC
    LYSENKO, Z
    JOULLIE, MM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (25) : 7505 - 7510
  • [27] DIPHENYLPHOSPHORYL AZIDE - NEW CONVENIENT REAGENT FOR A MODIFIED CURTIUS REACTION AND FOR PEPTIDE SYNTHESIS
    SHIOIRI, T
    YAMADA, S
    NINOMIYA, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6203 - &
  • [28] TOTAL SYNTHESIS OF THE CYTOTOXIC MACROCYCLE (+)-HITACHIMYCIN
    SMITH, AB
    RANO, TA
    CHIDA, N
    SULIKOWSKI, GA
    WOOD, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8008 - 8022
  • [29] Effects of catalysts on the cyclization of 2-diazo-2-methoxycarbonyl-N-aryl-N-alkylethanamides
    Smith, K
    Bahzad, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (23): : 2793 - 2798
  • [30] *TEXSAN, 1992, CRYST STRUCT AN PACK