SYNTHESIS OF OXYGEN-BRIDGED ANTIGESTAGENS

被引:4
|
作者
CLEVE, A
OTTOW, E
NEEF, G
WIECHERT, R
机构
[1] Research Laboratories, Schering AG
关键词
ANTIGESTAGENS; 11-BETA-SUBSTITUTED STEROIDS; 10,11-BETA-(OXY-1,2-PHENYLENE)-STEROIDS; ACID CATALYZED INTRAMOLECULAR EPOXIDE OPENING;
D O I
10.1016/S0040-4020(01)80365-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetic access to 10,11beta-(oxy-1,2-phenylene)-steroids 13 is described. Key steps are the S(N)2' type introduction of suitably ortho substituted arenes into vinyl epoxide 4, and ring closure by an acid catalysed intramolecular epoxide opening with the corresponding phenol. The resulting oxygen bridged steroids 13 are transformed into pharmacologically relevant progesterone antagonists 19a-c and 20.
引用
收藏
页码:2217 / 2226
页数:10
相关论文
共 50 条
  • [1] FORMATION OF OXYGEN-BRIDGED TETRAHYDROPYRIDINES IN THE HANTZSCH SYNTHESIS
    SHAH, AC
    REHANI, R
    ARYA, VP
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1994, (03): : 106 - 107
  • [2] SYNTHESIS AND CHARACTERIZATION OF AN OXYGEN-BRIDGED VANADIUM(III) DIMER
    CHANDRASEKHAR, P
    BIRD, PH
    [J]. INORGANIC CHEMISTRY, 1984, 23 (22) : 3677 - 3679
  • [3] Solid-phase synthesis of oxygen-bridged tetrahydropyridones
    Jönsson, D
    Erlandsson, M
    Undén, A
    [J]. TETRAHEDRON LETTERS, 2001, 42 (39) : 6953 - 6956
  • [4] Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs
    Alvarez, Lautaro D.
    Veleiro, Adriana S.
    Baggio, Ricardo F.
    Garland, Maria T.
    Edelsztein, Valeria C.
    Coirini, Hector
    Burton, Gerardo
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (07) : 3831 - 3838
  • [5] Synthesis of C(1)-C(11) oxygen-bridged pregnanes
    Veleiro, AS
    Taich, PJ
    Alvarez, LD
    Di Chenna, PH
    Burton, G
    [J]. TETRAHEDRON LETTERS, 2005, 46 (24) : 4235 - 4238
  • [6] EXTENDED OXYGEN-BRIDGED PYRIDINES AND PYRIMIDINES
    SVETLIK, J
    HANUS, V
    BELLA, J
    [J]. JOURNAL OF CHEMICAL RESEARCH, 1991, (01) : 4 - 5
  • [7] Synthesis and properties of oxygen-bridged aromatic polyesters based on isomeric naphthalenediols
    Choi, EJ
    Choi, BK
    Kim, JH
    Lee, SC
    Hill, DJT
    [J]. KOREA POLYMER JOURNAL, 2000, 8 (01): : 12 - 18
  • [8] SYNTHETIC APPROACHES TO OXYGEN-BRIDGED CYCLOOCTYL COMPOUNDS
    COPE, AC
    MCKERVEY, MA
    WEINSHEN.NM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (07): : 2229 - &
  • [9] STRUCTURAL STUDIES OF OXYGEN-BRIDGED IRON COMPOUNDS
    VASILEVSKY, I
    ROSE, NJ
    STENKAMP, RE
    [J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1992, 48 : 444 - 449
  • [10] Smectic bimetallomesogens: Synthesis and mesomorphic properties in oxygen-bridged dicopper and divanadyl complexes
    Leu, YF
    Lai, CK
    [J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1997, 44 (02) : 89 - 91