Total syntheses of the chlorinated β-carboline alkaloids bauerine A, B, and C

被引：16
|
作者：
Pohl, Berthold [1 ]
Luchterhandt, Thomas [1 ]
Bracher, Franz [1 ]
机构：
[1] Univ Munich, Ctr Drug Res, Dept Pharm, D-81377 Munich, Germany
来源：
SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 7-9期
关键词：
alkaloids; bauerine; cyclizations; dehydrogenations; 1-oxo-beta-carbolines;
D O I：
10.1080/00397910701226228
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first total synthesis of the chlorinated 1-oxo-/beta-carboline alkaloid bauerine C based on a Japp-Klingemann reaction is reported. An intermediate of this synthesis was converted to the fully aromatic beta-carboline bauerine B, and the related alkaloid bauerine A was prepared in an analogous manner.
引用
收藏
页码：1273 / 1280
页数：8
相关论文
共 50 条
  • [41] The biology and total syntheses of bisbenzylisoquinoline alkaloids
    Nguyen, Viviene K.
    Kou, Kevin G. M.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (35) : 7535 - 7543
  • [42] Total syntheses of crinine and related alkaloids
    Bru, Claire
    Guillou, Catherine
    TETRAHEDRON, 2006, 62 (38) : 9043 - 9048
  • [43] Enantioselective total syntheses of akuammiline alkaloids
    Morrill, Lucas
    Garg, Neil
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [44] Asymmetric Total Syntheses of Schizozygane Alkaloids
    Zhou, Wenqiang
    Zhou, Tao
    Tian, Mengxing
    Jiang, Yan
    Yang, Jiaojiao
    Lei, Shuai
    Wang, Qi
    Zhang, Chongzhou
    Qiu, Hanyue
    He, Ling
    Wang, Zhen
    Deng, Jun
    Zhang, Min
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (47) : 19975 - 19982
  • [45] THE TOTAL SYNTHESES OF (+/-)-RESERPINE AND RELATED ALKALOIDS
    MARTIN, SF
    BENAGE, B
    GRZEJSZCZAK, S
    RUEGER, H
    WILLIAMSON, SA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 189 (APR-): : 86 - ORGN
  • [46] TOTAL SYNTHESES OF LYCORINE AND RELATED ALKALOIDS
    TSUDA, Y
    ISOBE, K
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1976, 34 (09) : 625 - 640
  • [47] Spokewise Total Syntheses of Four Erythrina Alkaloids and Telescoped Syntheses of Six Additional Alkaloids
    Hu, Yue-Hong
    Gan, Zhang-Yan
    Li, Qin-Tong
    Chen, Yu-Ting
    Chen, Meng-En
    Zhang, Ling-Hui
    Zou, Jin-Chi
    Zhang, Fu-Min
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (19): : 14164 - 14176
  • [48] ENANTIOSELECTIVE TOTAL SYNTHESES OF INDOLIZIDINE ALKALOIDS (-)-205A AND (-)-235B
    POLNIASZEK, RP
    BELMONT, SE
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16): : 4868 - 4874
  • [49] Unified approach to the total syntheses of C10-functionalized lycopodium alkaloids
    Saha, Mrinmoy
    Carter, Rich G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [50] Biosynthetic Relationships and Total Syntheses of Naturally Occurring Benzo[c]Phenanthridine Alkaloids
    Bisai, Vishnumaya
    Shaheeda, M. K. Saina
    Gupta, Aditi
    Bisai, Alakesh
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (07) : 946 - 969
12345