SYNTHESIS OF 7,5-FUSED BICYCLIC LACTAMS BY STEREOSELECTIVE RADICAL CYCLIZATION

被引:36
|
作者
COLOMBO, L
DIGIACOMO, M
PAPEO, G
CARUGO, O
SCOLASTICO, C
MANZONI, L
机构
[1] UNIV PAVIA, DIPARTIMENTO CHIM GEN, I-27100 PAVIA, ITALY
[2] UNIV MILAN, DIPARTIMENTO CHIM ORGAN & IND, I-20133 MILAN, ITALY
关键词
D O I
10.1016/S0040-4039(00)76732-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
7,5-Fused bicyclic lactams of type 1 were synthesised by a route involving the radical cyclization of the intermediate 2. High level of stereoselection was obtained in this reaction.
引用
收藏
页码:4031 / 4034
页数:4
相关论文
共 50 条
  • [1] CONFORMATIONALLY CONSTRAINED DIPEPTIDES - SYNTHESIS OF 7,5-FUSED AND 6,5-FUSED BICYCLIC LACTAMS BY STEREOSELECTIVE RADICAL CYCLIZATIONS
    COLOMBO, L
    DIGIACOMO, M
    SCOLASTICO, C
    MANZONI, L
    BELVISI, L
    MOLTENI, V
    [J]. TETRAHEDRON LETTERS, 1995, 36 (04) : 625 - 628
  • [2] Improved synthesis of 7,5-fused bicyclic lactams for use as peptidomimetics
    Seide, W
    Watson, SE
    [J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (07) : 995 - 1002
  • [3] Novel extension of Meyers' methodology: Stereoselective construction of axially chiral 7,5-fused bicyclic lactams
    Penhoat, M
    Levacher, V
    Dupas, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24): : 9517 - 9520
  • [4] A convenient and versatile synthesis of 6,5-and 7,5-fused bicyclic lactams as peptidomimetics
    Zhang, XJ
    Jiang, W
    Schmitt, AC
    [J]. TETRAHEDRON LETTERS, 2001, 42 (30) : 4943 - 4945
  • [5] PEPTIDOMIMETIC SYNTHESIS - UTILIZATION OF N-ACYLIMINIUM ION CYCLIZATION CHEMISTRY IN THE GENERATION OF 7,6-FUSED AND 7,5-FUSED BICYCLIC LACTAMS
    ROBL, JA
    [J]. TETRAHEDRON LETTERS, 1994, 35 (03) : 393 - 396
  • [6] Synthesis of substituted conformationally constrained 6,5-and 7,5-fused bicyclic lactams as dipeptide mimics
    Artale, E
    Banfi, G
    Belvisi, L
    Colombo, L
    Colombo, M
    Manzoni, L
    Scolastico, C
    [J]. TETRAHEDRON, 2003, 59 (33) : 6241 - 6250
  • [7] Stereoselective synthesis of fused bicyclic β-lactams through radical cyclization of enyne-2-azetidinones
    Alcaide, B
    Rodríguez-Campos, IM
    Rodríguez-López, J
    Rodríguez-Vicente, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15): : 5377 - 5387
  • [8] Synthesis of 8,5-fused bicyclic lactam by stereo- and regioselective radical cyclization
    Manzoni, L
    Belvisi, L
    Scolastico, C
    [J]. SYNLETT, 2000, (09) : 1287 - 1288
  • [9] FREE-RADICAL CYCLIZATION IN THE SYNTHESIS OF FUSED BICYCLIC BETA-LACTAMS
    GIRIJAVALLABHAN, VM
    GANGULY, AK
    [J]. HETEROCYCLES, 1989, 28 (01) : 47 - 49
  • [10] SYNTHESIS OF BENZO-FUSED, 7,5-FUSED AND 7,6-FUSED AZEPINONES AS CONFORMATIONALLY RESTRICTED DIPEPTIDE MIMETICS
    ROBL, JA
    KARANEWSKY, DS
    ASAAD, MM
    [J]. TETRAHEDRON LETTERS, 1995, 36 (10) : 1593 - 1596