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
  • [11] Cytotoxic hybrids between the aromatic alkaloids bauerine C and rutaecarpine
    Huber, Kilian
    Bracher, Franz
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2007, 62 (10): : 1313 - 1316
  • [12] Enantioselective Total Syntheses of the Cephalotaxus Alkaloids (-)-Fortuneicyclidins A and B and (-)-Cephalotine B
    Sheng, Peng-Zhen
    Ni, Zhi-Bin
    Li, Lu-Lu
    Wei, Kun
    Zhang, Hongbin
    Yang, Yu-Rong
    ORGANIC LETTERS, 2023, 25 (41) : 7464 - 7469
  • [13] Enantioselective total syntheses of the cyclotryptamine alkaloids hodgkinsine and hodgkinsine B
    Kodanko, JJ
    Overman, LE
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (22) : 2528 - 2531
  • [14] Total syntheses of the benzodiazepine alkaloids circumdatin F and circumdatin C
    Witt, A
    Bergman, J
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08): : 2784 - 2788
  • [15] Total syntheses of amythiamicins A, B and C
    Nicolaou, K. C.
    Dethe, Dattatraya H.
    Chen, David Y. -K.
    CHEMICAL COMMUNICATIONS, 2008, (23) : 2632 - 2634
  • [16] TOTAL SYNTHESES OF STRYCHNOS ALKALOIDS
    KUEHNE, ME
    BROOK, CS
    XU, F
    PARSONS, R
    PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) : 2095 - 2098
  • [17] Total syntheses of arenamides A, B and C
    Chandrasekhar, Srivari
    Sathish, Kurapati
    Reddy, Gangireddy Pavan Kumar
    Mainkar, Prathama S.
    TETRAHEDRON-ASYMMETRY, 2014, 25 (04) : 348 - 355
  • [18] TOTAL SYNTHESES OF AMARYLLIDACEAE ALKALOIDS
    TSUDA, Y
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1981, 101 (04): : 295 - 321
  • [19] Total Syntheses of Herqulines B and C
    Zhu, Xu
    McAtee, Christopher C.
    Schindler, Corinna S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (08) : 3409 - 3413
  • [20] Total Syntheses of Herqulines B and C
    Zanda, Matteo
    Zhu, Xu
    McAtee, Christopher C.
    Schindler, C. S.
    SYNLETT, 2019, 30 (11) : A102 - A105
12345