Total synthesis of suaveoline and norsuaveoline via intramolecular oxazole-olefin Diels-Alder reaction

被引:36
作者
Ohba, M [1 ]
Natsutani, I
Sakuma, T
机构
[1] Kanazawa Univ, Adv Sci Res Ctr, Kanazawa, Ishikawa 9201192, Japan
[2] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
关键词
alkaloids; amino acids and derivatives; Diels-Alder reactions; indoles; oxazoles;
D O I
10.1016/j.tetlet.2004.06.108
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of two Rauwolfia alkaloids, suaveoline (1) and norsuaveoline (2), has been achieved through a highly stereoselective route starting from L-tryptophan methyl ester (9) and exploiting the intramolecular Diels-Alder reaction of the oxazole-olefin 16. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6471 / 6474
页数:4
相关论文
共 36 条
  • [1] THE ALKALOIDS OF RAUWOLFIA-VOLKENSII
    AKINLOYE, BA
    COURT, WE
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 1981, 4 (01) : 99 - 109
  • [2] ALKALOIDS OF RAUWOLFIA-NITIDA ROOT BARK
    AMER, MA
    COURT, WE
    [J]. PHYTOCHEMISTRY, 1981, 20 (11) : 2569 - 2573
  • [3] ROOT WOOD ALKALOIDS OF RAUWOLFIA-MACROPHYLLA
    AMER, MMA
    COURT, WE
    [J]. PLANTA MEDICA, 1981, 43 (01) : 94 - 95
  • [4] AMER MMA, 1980, PLANTA MED, P8
  • [5] New asymmetric route to bridged indole alkaloids: Formal enantiospecific syntheses of (-)-suaveoline, (-)-raumacline and (-)-N-b-methylraumacline
    Bailey, PD
    Collier, ID
    Hollinshead, SP
    Moore, MH
    Morgan, KM
    Smith, DI
    Vernon, JM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (08): : 1209 - 1214
  • [6] New asymmetric routes to ajmaline and suaveoline indole alkaloids
    Bailey, PD
    Morgan, KM
    Smith, DI
    Vernon, JM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21): : 3566 - 3577
  • [7] The total synthesis of (-)-suaveoline
    Bailey, PD
    Morgan, KM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (21): : 3578 - 3583
  • [8] DIASTEREOSELECTIVITY AND ENANTIOSELECTIVITY IN THE PICTET-SPENGLER REACTION
    BAILEY, PD
    HOLLINSHEAD, SP
    MCLAY, NR
    MORGAN, K
    PALMER, SJ
    PRINCE, SN
    REYNOLDS, CD
    WOOD, SD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04): : 431 - 439
  • [9] USE OF THE KINETICALLY CONTROLLED PICTET-SPENGLER REACTION IN THE ASYMMETRIC-SYNTHESIS OF INDOLE ALKALOIDS - FORMAL SYNTHESES OF (-)-AJMALINE, (-)-KOUMINE, (-)-TABERPSYCHINE, (-)-KOUMIDINE AND (-)-SUAVOLINE
    BAILEY, PD
    MCLAY, NR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04): : 441 - 449
  • [10] Batista CVF, 1996, PHYTOCHEMISTRY, V41, P969, DOI 10.1016/0031-9422(95)00666-4