PSEUDODISTOMIN-C, A NEW PIPERIDINE ALKALOID WITH UNUSUAL ABSOLUTE-CONFIGURATION FROM THE OKINAWAN TUNICATE PSEUDODISTOMA-KANOKO

被引:47
|
作者
KOBAYASHI, J
NAITOH, K
DOI, Y
DEKI, K
ISHIBASHI, M
机构
[1] Faculty of Pharmaceutical Sciences, Hokkaido University
来源
JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 21期
关键词
D O I
10.1021/jo00126a053
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.
引用
收藏
页码:6941 / 6945
页数:5
相关论文
共 17 条
  • [1] REVISED STRUCTURE OF PSEUDODISTOMIN-A, A PIPERIDINE ALKALOID ISOLATED FROM THE OKINAWAN TUNICATE PSEUDODISTOMA-KANOKO
    ISHIBASHI, M
    DEKI, K
    KOBAYASHI, J
    JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (05): : 804 - 806
  • [2] PSEUDODISTOMIN-A AND PSEUDODISTOMIN-B, NOVEL ANTINEOPLASTIC PIPERIDINE ALKALOIDS WITH CALMODULIN ANTAGONISTIC ACTIVITY FROM THE OKINAWAN TUNICATE PSEUDODISTOMA-KANOKO
    ISHIBASHI, M
    OHIZUMI, Y
    SASAKI, T
    NAKAMURA, H
    HIRATA, Y
    KOBAYASHI, J
    JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03): : 450 - 453
  • [3] Total synthesis of pseudodistomin C, a sphingosine-related piperidine alkaloid from tunicate Pseudodistoma kanoko
    Doi, YK
    Ishibashi, M
    Kobayashi, J
    TETRAHEDRON, 1996, 52 (13) : 4573 - 4580
  • [4] Total synthesis of pseudodistomin C, a sphingosine-related piperidine alkaloid from tunicate Pseudodistoma kanoko
    Doi, Y.
    Ishibashi, M.
    Kobayashi, J.
    Tetrahedron, 52 (13):
  • [5] Obscuraminols, new unsaturated amino alcohols from the tunicate Pseudodistoma obscurum:: structure and absolute configuration
    Garrido, L
    Zubía, E
    Ortega, MJ
    Naranjo, S
    Salvá, J
    TETRAHEDRON, 2001, 57 (21) : 4579 - 4588
  • [6] STRUCTURE AND ABSOLUTE-CONFIGURATION OF MYRINE, A NEW QUINOLIZIDINE ALKALOID FROM VACCINIUM-MYRTILLUS
    SLOSSE, P
    HOOTELE, C
    TETRAHEDRON LETTERS, 1978, (04) : 397 - 398
  • [7] STRUCTURE AND ABSOLUTE-CONFIGURATION OF DELPHISINE - NEW DITERPENE ALKALOID FROM DELPHINIUM-STAPHISAGRIA
    PELLETIER, SW
    DECAMP, WH
    LAJSIC, SD
    DJARMATI, Z
    KAPADI, AH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) : 7815 - 7817
  • [8] DETERMINATION OF ABSOLUTE-CONFIGURATION AND PREFERRED CONFORMATION OF LINDENIANINE, A NEW ALKALOID FROM LUPINUS-LINDENIANUS
    NAKANO, T
    CASTALDI, A
    MORALES, A
    ACTA CIENTIFICA VENEZOLANA, 1973, 24 : 72 - 72
  • [9] THE ABSOLUTE-CONFIGURATION OF TSUKUSHINAMINE-A - A NEW CAGE-TYPE LUPIN ALKALOID FROM SOPHORA-FRANCHETIANA
    BORDNER, J
    OHMIYA, S
    OTOMASU, H
    HAGINIWA, J
    MURAKOSHI, I
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1980, 28 (06) : 1965 - 1968
  • [10] STRUCTURE AND ABSOLUTE-CONFIGURATION OF KHUSITONEOL, A NEW KETOALCOHOL-C-14 FROM VETIVER OIL
    KALSI, PS
    ARORA, GS
    CHHINA, K
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1985, 24 (05): : 496 - 498