TOTAL SYNTHESIS OF (-)-QUINOCARCIN AND (-)-10-DECARBOXYQUINOCARCIN

被引:23
作者
KATOH, T [1 ]
KIRIHARA, M [1 ]
NAGATA, Y [1 ]
KOBAYASHI, Y [1 ]
ARAI, K [1 ]
MINAMI, J [1 ]
TERASHIMA, S [1 ]
机构
[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN
关键词
TOTAL SYNTHESIS; QUINOCARCIN; 10-DECARBOXYQUINOCARCIN; ANTITUMOR ANTIBIOTIC; ALDOL COUPLING; DIASTEREOSELECTIVE REDUCTION; INTERMOLECULAR AMINAL FORMATION;
D O I
10.1016/S0040-4039(00)73850-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title total synthesis was accomplished by employing diastereoselective reduction of 1, 3-disubstituted isoquinolines as a key step. The cytotoxicity of 10-decarboxyquinocarcin and its 7-cyano congeners were found to be 10-1000 times more potent than those of quinocarcin and its 7-cyano congeners against P388 murine leukemia.
引用
收藏
页码:5747 / 5750
页数:4
相关论文
共 14 条
  • [1] TOTAL SYNTHESES OF PHLEICHROME, CALPHOSTIN-A, AND CALPHOSTIN-D - UNUSUAL STEREOSELECTIVE AND STEREOSPECIFIC REACTIONS IN THE SYNTHESIS OF PERYLENEQUINONES
    BROKA, CA
    [J]. TETRAHEDRON LETTERS, 1991, 32 (07) : 859 - 862
  • [2] REACTIONS OF THE CARBANION FROM AN ORSELLINATE DERIVATIVE WITH ELECTROPHILES
    CARPENTER, TA
    EVANS, GE
    LEEPER, FJ
    STAUNTON, J
    WILKINSON, MR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05): : 1043 - 1051
  • [3] STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-QUINOCARCIN
    FUKUYAMA, T
    NUNES, JJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (15) : 5196 - 5198
  • [4] ASYMMETRIC-SYNTHESIS OF (-)-QUINOCARCIN
    GARNER, P
    HO, WB
    SHIN, HW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) : 2767 - 2768
  • [5] SELECTIVE SYNTHESIS OF MONOMETHYLTOCOLS VIA ETA-ALLYLNICKEL COMPLEXES
    INOUE, S
    SAITO, K
    KATO, K
    NOZAKI, S
    SATO, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (18): : 2097 - 2101
  • [6] TOTAL SYNTHESIS OF (-)-QUINOCARCIN AND (-)-10-DECARBOXYQUINOCARCIN
    KATOH, T
    KIRIHARA, M
    NAGATA, Y
    KOBAYASHI, Y
    ARAI, K
    MINAMI, J
    TERASHIMA, S
    [J]. TETRAHEDRON LETTERS, 1993, 34 (36) : 5747 - 5750
  • [7] EFFICIENT AND SELECTIVE CLEAVAGE OF ACETALS AND KETALS USING FERRIC-CHLORIDE ADSORBED ON SILICA-GEL
    KIM, KS
    SONG, YH
    LEE, BH
    HAHN, CS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (03) : 404 - 407
  • [8] 4-O-BENZYL-2,3-O-ISOPROPYLIDENE-L-THREOSE - A NEW AND USEFUL BUILDING BLOCK FOR THE SYNTHESES OF L-SUGARS
    MUKAIYAMA, T
    SUZUKI, K
    YAMADA, T
    [J]. CHEMISTRY LETTERS, 1982, (06) : 929 - 932
  • [9] SAITO H, 1990, CHEM PHARM BULL, V38, P1278
  • [10] SYNTHETIC APPROACH TO QUINOCARCIN
    SAITO, H
    HIRATA, T
    [J]. TETRAHEDRON LETTERS, 1987, 28 (35) : 4065 - 4068