A rapid stereocontrolled synthesis of the 3a-hydroxy-pyrrolo[2,3-b]indole skeleton, a building block for 10b-hydroxy-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4-diones

被引：53
|
作者：
Ley, SV [1 ]
Cleator, E [1 ]
Hewitt, PR [1 ]
机构：
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2003年 / 1卷 / 20期
关键词：
5-N-ACETYLARDEEMIN; OXYGENATION; DERIVATIVES; TRYPTOPHAN; AMAUROMINE;
D O I：
10.1039/b308288a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A two-step selenocyclisation-oxidative deselenation sequence was used to establish the 3a-hydroxy-pyrrolo-[2,3-b]indole core; these tricycles were used as effective precursors to 10b-hydroxy-pyrazino[1',2' : 1,5]pyrrolo-[2,3-b]indole-1,4-diones.
引用
收藏
页码：3492 / 3494
页数：3
相关论文
共 50 条
  • [1] 4-Phenylsulfonyl-2-(p-tolylsulfonyl)-1H,8H-pyrrolo[2,3-b]indole
    Badenock, Jeanese C.
    Jordan, Jason A.
    Pelkey, Erin T.
    Gribble, Gordon W.
    Jasinski, Jerry P.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O2757 - U2073
  • [2] Base-catalyzed cascade synthesis of 2,3-dihydrofuro[2,3-b]pyridines and 2,3-dihydro-1H- pyrrolo[2,3-b]pyridines from N-propargylic β-enaminones
    Yang, Xiaobing
    Hu, Fangzhong
    Wang, Yang
    Yang, Chiming
    Zou, Xiaomao
    Liu, Jiahui
    Zhang, Qichun
    CHEMICAL COMMUNICATIONS, 2017, 53 (54) : 7497 - 7500
  • [3] A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones
    Jones, Alan M.
    Patterson, Stephen
    Lorion, Magali M.
    Slawin, Alexandra M. Z.
    Westwood, Nicholas J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (38) : 8998 - 9011
  • [4] Selective Synthesis of Cyclopeptides with a 2-Oxindole or 3a-Hydroxy-hexahydropyrrolo-[2,3-b]indole Structure by Cytochrome P450 Enzymes
    Li, Chao
    Ma, Junying
    Guo, Lu
    Xu, Chao
    Zhong, Zijian
    Li, Pengwei
    Tang, Yue
    Wang, Wenzhao
    Li, Defeng
    Ye, Tao
    Guo, Zhengyan
    Chen, Yihua
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (04) : 3304 - 3314
  • [5] Design, synthesis and molecular docking of novel 4-morpholino-1H-pyrrolo [2,3-b] pyridine-5-carboxamides and 4-methylpiperazin-1H-pyrrolo[2,3-b] pyridine-5-carboxamides for the evaluation anti-cancer activity
    Mothe, Thirupathi
    Lingala, Arun Kumar
    Konkala, Veera Swamy
    Murahari, Kiran Kumar
    Gopala, Sridhar Goud
    Desireddi, Janardana Reddi
    Manchal, Ravinder
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1311
  • [6] Synthesis of 2,6-disubstituted pyrido[2,3-b][1,4]oxazines
    Nishiwaki, Nagatoshi
    Hisaki, Masataka
    Ono, Masaki
    Ariga, Masahiro
    TETRAHEDRON, 2009, 65 (36) : 7403 - 7407
  • [7] Synthesis of a Novel Heterocyclic System - Pyrimido[5′,4′/5,6]thiopyrano [2,3-b]indole
    Sudzius, Jurgis
    Tumkevicius, Sigitas
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (07) : 526 - 528
  • [8] Novel 1-aminoethyl-3-arylsulfonyl-1H-pyrrolo[2,3-b]pyridines are potent 5-HT6 agonists
    Bernotas, Ronald C.
    Lenicek, Steven
    Antane, Schuyler
    Cole, Derek C.
    Harrison, Boyd L.
    Robichaud, Albert J.
    Zhang, Guo Ming
    Smith, Deborah
    Platt, Brian
    Lin, Qian
    Li, Ping
    Coupet, Joseph
    Rosenzweig-Lipson, Sharon
    Beyer, Chad E.
    Schechter, Lee E.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (14) : 5153 - 5163
  • [9] Synthesis of 3-Substituted 2-Aminonaphtho[2,3-b]furan-4,9-diones from 2-Hydroxy-1,4-Naphthoquinone and Nitroalkenes
    Zanwar, Manoj R.
    Kavala, Veerababurao
    Gawande, Sachin D.
    Kuo, Chun-Wei
    Kuo, Ting-Shen
    Chen, Mei-Ling
    He, Chiu-Hui
    Yao, Ching-Fa
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (36) : 8288 - 8298
  • [10] First synthesis of tert-butyl-substituted [1,2,4]triazino[5,6-b]indole-3-thiols and indolo[2,3-b]quinoxalines
    Lv, Mingyue
    Zheng, Hongmei
    Li, Yang
    Gao, Wentao
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (10) : 6927 - 6939
12345