SYNTHESIS OF (-)-CHANOCLAVINE-I

被引:26
作者
KARDOS, N [1 ]
GENET, JP [1 ]
机构
[1] ECOLE NATL SUPER CHIM,CNRS,SYNTH ORGAN LAB,F-75231 PARIS 05,FRANCE
关键词
D O I
10.1016/0957-4166(94)80122-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The total enantioselective synthesis of (-)-chanoclavine I 2 in twelve steps from indole-4-carboxaldehyde 4 is described The key-step 3 --> 6 which involves the formation of the C ring by creation of the C5-C10 bond is catalyzed by a chiral palladium (0) complexes. The chiral ergoline synthon 6 is produced with an excellent diastereo-and enantioselectivity (up to 95%) eel.
引用
收藏
页码:1525 / 1533
页数:9
相关论文
共 75 条
  • [1] BICYCLIC AND TRICYCLIC ERGOLINE PARTIAL STRUCTURES - RIGID 3-(2-AMINOETHYL)PYRROLES AND 3-(2-AMINOETHYL)PYRAZOLE AND 4-(2-AMINOETHYL)PYRAZOLE AS DOPAMINE AGONISTS
    BACH, NJ
    KORNFELD, EC
    JONES, ND
    CHANEY, MO
    DORMAN, DE
    PASCHAL, JW
    CLEMENS, JA
    SMALSTIG, EB
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (05) : 481 - 491
  • [2] BATCHO AD, 1976, Patent No. 3976639
  • [3] BERDE B, 1978, HDB EXPT PHARM, V49
  • [4] BOVE FJ, 1970, STORY ERGOT
  • [5] REAKTIONSFAHIGE SAUREAMID-DIMETHYLSULFAT-KOMPLEXE
    BREDERECK, H
    EFFENBERGER, F
    SIMCHEN, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1961, 73 (14) : 493 - &
  • [6] BUCHI G, 1977, J ORG CHEM, V42, P1784
  • [7] CLEMENS JA, 1977, J MED CHEM, V20, P1473
  • [8] FEHR T, 1966, J CHEM SOC CHEM COMM, P801
  • [9] BIOSYNTHESIS OF ERGOT ALKALOIDS AND RELATED COMPOUNDS
    FLOSS, HG
    [J]. TETRAHEDRON, 1976, 32 (08) : 873 - 912
  • [10] INFLUENCE OF ERGOT ALKALOIDS ON PITUITARY PROLACTIN AND PROLACTIN-DEPENDENT PROCESSES
    FLOSS, HG
    CASSADY, JM
    ROBBERS, JE
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1973, 62 (05) : 699 - 715