Intramolecular Diels-Alder reaction for the synthesis of tetracyclic carbazoles and isocanthines

被引:20
|
作者
Naik, Prajakta N. [1 ]
Khan, Ayesha [1 ]
Kusurkar, Radhika S. [1 ]
机构
[1] Univ Pune, Dept Chem, Pune 411007, Maharashtra, India
关键词
Intramolecular Diels-Alder reaction; Isocanthine; Tetracyclic carbazole; alpha; beta-Unsaturated hydrazone; CANTHINE ANALOGS; ARYLATION; ROUTE;
D O I
10.1016/j.tet.2013.10.054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One pot intramolecular Diels-Alder reaction has been efficiently used as a new route for the synthesis of four tetracyclic carbazoles and four isocanthine analogues where a dialdehyde is utilised as a common intermediate for both the scaffolds. Biological activity was evaluated for some molecules, which demonstrated moderate activity against HeLa cervical cancer cell lines (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10733 / 10738
页数:6
相关论文
共 50 条
  • [41] AN INTRAMOLECULAR IMMONIUM ION VARIATION OF THE DIELS-ALDER REACTION - SYNTHESIS OF (+/-)-DIHYDROCANNIVONINE
    GRIECO, PA
    LARSEN, SD
    JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (18): : 3553 - 3555
  • [42] AN INTRAMOLECULAR DIELS-ALDER REACTION - A SIMPLE SYNTHESIS OF GAMMA-APOPICROPODOPHYLLIN
    KLEMM, LH
    GOPINATH, KW
    TETRAHEDRON LETTERS, 1963, (19) : 1243 - 1245
  • [43] SYNTHESIS OF INDOLIZIDINE ALKALOIDS VIA THE INTRAMOLECULAR IMINO DIELS-ALDER REACTION
    KHATRI, NA
    SCHMITTHENNER, HF
    SHRINGARPURE, J
    WEINREB, SM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (21) : 6387 - 6393
  • [44] Asymmetric Total Synthesis of Caribenol A via an Intramolecular Diels-Alder Reaction
    Han, Jing-Chun
    Liu, Lian-Zhu
    Chang, Yuan-Yuan
    Yue, Guo-Zong
    Guo, Jie
    Zhou, Li-Yan
    Li, Chuang-Chuang
    Yang, Zhen
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (11): : 5492 - 5504
  • [45] Intramolecular Imino Diels-Alder Reaction: Progress toward the Synthesis of Uncialamycin
    Desrat, Sandy
    van de Weghe, Pierre
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17): : 6728 - 6734
  • [46] A SIMPLIFIED TOTAL SYNTHESIS OF CYTOCHALASINS VIA AN INTRAMOLECULAR DIELS-ALDER REACTION
    STORK, G
    NAKAMURA, E
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (16) : 5510 - 5512
  • [47] Synthesis of the tricyclic core of vinigrol via an intramolecular Diels-Alder reaction
    Grise, Christiane M.
    Tessier, Guillaume
    Barriault, Louis
    ORGANIC LETTERS, 2007, 9 (08) : 1545 - 1548
  • [48] PERICYCLIZATION OF VINYLALLENES IN ORGANIC-SYNTHESIS - ON THE INTRAMOLECULAR DIELS-ALDER REACTION
    OKAMURA, WH
    CURTIN, ML
    SYNLETT, 1990, (01) : 1 - 9
  • [49] Taxane synthesis: The intramolecular Diels-Alder approach
    Winkler, JD
    Bhattacharya, SK
    Liotta, F
    Batey, RA
    Kim, HS
    Saraiva, M
    Chandramouli, SV
    Kelly, RC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 47 - ORGN
  • [50] Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy
    Cowell, Joseph
    Abualnaja, Matokah
    Morton, Stephanie
    Linder, Ruth
    Buckingham, Faye
    Waddell, Paul G.
    Probert, Michael R.
    Hall, Michael J.
    RSC ADVANCES, 2015, 5 (21) : 16125 - 16152