Carbazomycin G: Method Development and Total Synthesis

被引:6
|
作者
Elumalai, Vijayaragavan [1 ]
Gambarotti, Cristian [2 ]
Bjorsvik, Hans-Rene [1 ]
机构
[1] Univ Bergen, Dept Chem, Allegaten 41, N-5007 Bergen, Norway
[2] Politecn Milan, Dept Chem Mat & Chem Engn, Piazza Leonardo da Vinci 32, I-20133 Milan, Italy
关键词
Synthetic methods; Total synthesis; Cross-coupling; C-H activation; C-N bond formation; Redox reactions; TRANSITION-METAL-COMPLEXES; 1ST TOTAL-SYNTHESIS; ORGANIC-SYNTHESIS; DIENE COMPLEXES; BIOLOGICAL EVALUATION; SELECTIVE REDUCTION; REDUCING AGENT; ANTIBIOTICS; ALKALOIDS; EFFICIENT;
D O I
10.1002/ejoc.201800359
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel total synthesis leading to the carbazole alkaloid carbazomycin G was designed and developed. The outlined synthetic route is composed of twelve synthetic steps including the transformations of the initial simple substrate and intermediates. To realize the designed synthesis, in total six new synthetic methods were developed and implemented to provide the target molecule in an overall yield of 8.3%.
引用
收藏
页码:1984 / 1992
页数:9
相关论文
共 50 条
  • [1] Total Synthesis of Carbazomycin G
    Chakraborty, Suchandra
    Saha, Chandan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (25) : 5731 - 5736
  • [2] A novel total synthesis of antibiotic carbazole alkaloid carbazomycin G
    Hagiwara, H
    Choshi, T
    Fujimoto, H
    Sugino, E
    Hibino, S
    TETRAHEDRON, 2000, 56 (32) : 5807 - 5811
  • [3] First total synthesis of carbazomycin C and D
    Knolker, HJ
    Schlechtingen, G
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04): : 349 - 350
  • [4] Palladium-catalyzed total synthesis of the antibiotic carbazole alkaloids carbazomycin G and H
    Knölker, HJ
    Fröhner, W
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (02): : 173 - 175
  • [5] Transition metal complexes in organic synthesis .38. First total synthesis of carbazomycin G and H
    Knolker, HJ
    Frohner, W
    TETRAHEDRON LETTERS, 1997, 38 (23) : 4051 - 4054
  • [6] Total Synthesis of Carbazomycin G by a Thermal Ring Expansion/Self-Redox Reaction Cascade
    An, Yong
    Wang, Yunxia
    Hu, Xiangdong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3715 - 3718
  • [7] THE NEW APPROACH TO ANTIBIOTIC CARBAZOMYCINS - THE FORMAL TOTAL SYNTHESIS OF CARBAZOMYCIN-A AND CARBAZOMYCIN-B
    HIBINO, S
    TONARI, A
    CHOSHI, T
    SUGINO, E
    HETEROCYCLES, 1993, 35 (01) : 441 - 444
  • [8] THE TOTAL SYNTHESIS OF THE CARBAZOLE ANTIBIOTIC CARBAZOMYCIN-B AND AN IMPROVED ROUTE TO CARBAZOMYCIN-A1B
    KNOLKER, HJ
    BAUERMEISTER, M
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (19) : 1468 - 1470
  • [9] A Cyclobutanol Ring-Expansion Approach to Oxygenated Carbazoles: Total Synthesis of Glycoborine, Carbazomycin A and Carbazomycin B
    Natho, Philipp
    Allen, Lewis A. T.
    Parsons, Philip J.
    SYNLETT, 2023, 34 (08) : 937 - 942
  • [10] CARBAZOMYCIN-G AND CARBAZOMYCIN-H, NOVEL CARBAZOMYCIN-CONGENERS CONTAINING A QUINOL MOIETY
    KANEDA, M
    NAID, T
    KITAHARA, T
    NAKAMURA, S
    HIRATA, T
    SUGA, T
    JOURNAL OF ANTIBIOTICS, 1988, 41 (05): : 602 - 608