Synthesis and antitumor activity of puupehedione and related compounds

被引:79
作者
Barrero, AF [1 ]
Alvarez-Manzaneda, EJ
Chahboun, R
Cortés, M
Armstrong, V
机构
[1] Univ Granada, Fac Ciencias, Dept Quim Organ, E-18071 Granada, Spain
[2] Pontificia Univ Catolica Chile, Fac Quim, Dept Quim Organ, Santiago 22, Chile
关键词
terpenes; antitumour compounds; marine metabolites;
D O I
10.1016/S0040-4020(99)00992-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first enantiospecific synthesis of bioactive marine puupehedione (2) and related compounds from (-)-sclanol (11) is reported. The antitumor activity of these compounds was assayed and compared with that of the natural products. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:15181 / 15208
页数:28
相关论文
共 14 条
  • [1] Synthesis of monoterpenic analogues of puupehenone and puupehedione
    Barrero, AF
    Alvarez-Manzaneda, EJ
    Herrador, MM
    Valdivia, MV
    Chahboun, R
    [J]. TETRAHEDRON LETTERS, 1998, 39 (16) : 2425 - 2428
  • [2] SYNTHESIS OF BIOLOGICALLY-ACTIVE DRIMANES AND HOMODRIMANES FROM (-)-SCLAREOL
    BARRERO, AF
    MANZANEDA, EA
    ALTAREJOS, J
    SALIDO, S
    RAMOS, JM
    SIMMONDS, MSJ
    BLANEY, WM
    [J]. TETRAHEDRON, 1995, 51 (27) : 7435 - 7450
  • [3] Synthesis of wiedendiol-A and wiedendiol-B from labdane diterpenes
    Barrero, AF
    Alvarez-Manzaneda, EJ
    Chahboun, R
    [J]. TETRAHEDRON, 1998, 54 (21) : 5635 - 5650
  • [4] Enantiospecific synthesis of (+)-puupehenone from (-)-sclareol and protocatechualdehyde
    Barrero, AF
    AlvarezManzaneda, EJ
    Chahboun, R
    [J]. TETRAHEDRON LETTERS, 1997, 38 (13) : 2325 - 2328
  • [5] Enantiospecific synthesis of wiedendiol-B from (-)-sclareol and (+)-cis-abienol
    Barrero, AF
    AlvarezManzaneda, EJ
    Chahboun, R
    [J]. TETRAHEDRON LETTERS, 1997, 38 (46) : 8101 - 8104
  • [6] SYNTHESIS OF BIOLOGICALLY-ACTIVE DRIMANES FROM (-)-SCLAREOL
    BARRERO, AF
    ALVAREZMANZANEDA, E
    ALTAREJOS, J
    SALIDO, S
    RAMOS, JM
    [J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2945 - 2948
  • [7] ANTINEOPLASTIC AND ANTIHERPETIC ACTIVITY OF SPERMIDINE CATECHOLAMIDE IRON CHELATORS
    BERGERON, RJ
    CAVANAUGH, PF
    KLINE, SJ
    HUGHES, RG
    ELLIOTT, GT
    PORTER, CW
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 121 (03) : 848 - 854
  • [8] NOVEL INHIBITORS OF CHOLESTERYL ESTER TRANSFER PROTEIN
    CHACKALAMANNIL, S
    XIA, Y
    WANG, YG
    TSAI, HG
    CZARNIECKI, M
    WANG, S
    CLEMMONS, A
    AHN, HS
    BOYKOW, G
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (17) : 2005 - 2010
  • [9] WIEDENDIOL-A AND WIEDENDIOL-B, CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITORS FROM THE MARINE SPONGE XESTOSPONGLIA-WIEDENMAYERI
    COVAL, SJ
    CONOVER, MA
    MIERZWA, R
    KING, A
    PUAR, MS
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (06) : 605 - 610
  • [10] Faulkner DJ, 1998, NAT PROD REP, V15, P113