Diastereospecific synthesis of ketooxindoles. Potential intermediates for the synthesis of alstonisine as well as for Voachalotine related oxindole alkaloids

被引:23
作者
Yu, P [1 ]
Cook, JM [1 ]
机构
[1] UNIV WISCONSIN,DEPT CHEM,MILWAUKEE,WI 53201
关键词
D O I
10.1016/S0040-4039(97)10420-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient method has been developed to convert N-a-H tetracyclicketone Ia into the two corresponding oxindoles[C(7)] diastereospecifically. Treatment of the N-a-H, N-b-benzyl tetracyclicketone la with t-BuOCl provided diastereomer 2a (related to Voacanga oxindoles), whereas the same process with N-b-H (Ib) or N-b-benzoyl (Ic) substituted analogs funished the diastereomers 2b and 2c (related to alstonisine), respectively. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8799 / 8802
页数:4
相关论文
共 14 条
  • [1] BRAEKMAN JC, 1969, B SOC CHIM BELG, V78, P523
  • [2] ALSTONIA ALKALOIDS .11. ALKALOIDS OF ALSTONIA-MUELLERIANA
    ELDERFIE.RC
    GILMAN, RE
    [J]. PHYTOCHEMISTRY, 1972, 11 (01) : 339 - &
  • [3] BIOMIMETIC TRANSFORMATIONS AMONG MONOMERIC MACROLINE-RELATED INDOLE ALKALOIDS
    GARNICK, RL
    LEQUESNE, PW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) : 4213 - 4219
  • [4] ALKALOIDS OF ALSTONIA-ANGUSTIFOLIA
    GHEDIRA, K
    ZECHESHANROT, M
    RICHARD, B
    MASSIOT, G
    MENOLIVIER, LL
    SEVENET, T
    GOH, SH
    [J]. PHYTOCHEMISTRY, 1988, 27 (12) : 3955 - 3962
  • [5] HARADA M, 1978, CHEM PHARM BULL, V26, P48
  • [6] HOLLINSHEAD SP, 1989, HETEROCYCLES, V29, P529
  • [7] TOTAL SYNTHESIS OF INDOLE AND DIHYDROINDOLE ALKALOIDS .8. STUDIES ON SYNTHESIS OF BISINDOLE ALKALOIDS IN VINBLASTINE-VINCRISTINE SERIES - CHLOROINDOLENINE APPROACH
    KUTNEY, JP
    BECK, J
    BYLSMA, F
    COOK, J
    CRETNEY, WJ
    FUJI, K
    IMHOF, R
    TREASURYWALA, AM
    [J]. HELVETICA CHIMICA ACTA, 1975, 58 (06) : 1690 - 1719
  • [8] INTERPRETATION OF PATTERSON FUNCTION OF CRYSTALS CONTAINING A KNOWN MOLECULAR FRAGMENT - STRUCTURE OF AN ALSTONIA ALKALOID
    NORDMAN, CE
    NAKATSU, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (03) : 353 - &
  • [9] STUDIES DIRECTED TOWARD THE ENANTIOSPECIFIC SYNTHESIS OF GARDNERIA, VOACANGA, AND ALSTONIA OXINDOLE ALKALOIDS
    PETERSON, AC
    COOK, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) : 120 - 129
  • [10] RAHMAN A, 1987, PHYTOCHEMISTRY, V26, P865