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
  • [21] BETA-CARBOLINE ALKALOIDS .1. SYNTHESES OF 1-ARYL-BETA-CARBOLINE AND 1-ALKENYL-BETA-CARBOLINE BY PALLADIUM-CATALYZED COUPLING REACTIONS
    BRACHER, F
    HILDEBRAND, D
    LIEBIGS ANNALEN DER CHEMIE, 1992, (12): : 1315 - 1319
  • [22] TOTAL SYNTHESES OF THE NATURAL-PRODUCTS FROM ALKALOIDS TO TERPENES
    BAN, Y
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1993, 51 (02) : 111 - 127
  • [23] Collective Total Syntheses of Atisane-Type Diterpenes and Atisine-Type Diterpenoid Alkaloids: (±)-Spiramilactone B, (±)-Spiraminol, (±)-Dihydroajaconine, and (±)-Spiramines C and D
    Cheng, Hang
    Zeng, Fan-Hao
    Yang, Xue
    Meng, Yin-Juan
    Xu, Liang
    Wang, Feng-Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (01) : 392 - 396
  • [24] Enantioselective Total Syntheses of Communesins A and B
    Zuo, Zhiwei
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) : 12008 - 12011
  • [25] Total Syntheses of Lycopodium Alkaloids (+)-Fawcettimine, (+)-Fawcettidine, and (-)-8-Deoxyserratinine
    Li, Houhua
    Wang, Xiaoming
    Lei, Xiaoguang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) : 491 - 495
  • [26] Securinega Alkaloids: Complex Structures, Potent Bioactivities, and Efficient Total Syntheses
    Wehlauch, Robin
    Gademann, Karl
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (09) : 1146 - 1159
  • [27] Asymmetric Total Syntheses of Macroline-Type Alkaloids Alstomicine and Alstofolinine A
    Wei, Kai
    Hu, Wen
    Sun, Yucui
    Zhu, Tuo
    Chen, Wen
    Zhang, Hongbin
    SYNTHESIS-STUTTGART, 2023, 55 (17): : 2648 - 2657
  • [28] Total Syntheses of Hosieines A-C
    Zhang, Jiayang
    Yan, Xu
    Zhang, Qing-Bao
    Wang, Fang
    Yang, Bin
    Yang, Yang
    ADVANCED SCIENCE, 2024, 11 (14)
  • [29] Divergent Total Syntheses of (-)-Daphnezomines A and B and (+)-Dapholdhamine B
    Su, Shaobin
    Lin, Chengcheng
    Zhai, Hongbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (23)
  • [30] Asymmetric Total Syntheses of (+)-Penostatins A and C
    Wang, Jian
    Marquez-Cadena, Miguel Adrian
    Tong, Rongbiao
    ORGANIC LETTERS, 2020, 22 (13) : 5074 - 5078
12345