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
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
  • [41] ACETALS OF LACTAMS AND ACIDAMIDES .19. SYNTHESIS OF 3-CYANO-6-DIMETHYL-AMINOPYRIDONE-2 AND PYRROLO[2,3-B]PYRIDINE, PYRIDO[2,3-B]PYRIDINE AND AZEPINO[2,3-B]PYRIDINE DERIVATIVES
    GRANIK, VG
    BELYAYEVA, OY
    GLUSHKOV, RG
    VLASOVA, TF
    ANISIMOVA, OS
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1977, (08): : 1106 - 1109
  • [42] 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
  • [43] Synthesis of a novel heterocyclic system: Quinoxalino[1,2-a]pyrrolo-[2,3-b][1,5] benzothiazepine [4]
    Maslivets, A.N.
    Bozdyreva, K.S.
    Chemistry of Heterocyclic Compounds, 2002, 38 (12) : 1535 - 1536
  • [44] Synthesis of 2,3-Disubstituted 5-Iodo-1H-Pyrrolo[2,3-b]pyridines via Fischer Cyclization
    Alekseyev, Roman S.
    Amirova, Sabina S.
    Terenin, Vladimir I.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (05) : 2656 - 2663
  • [45] SYNTHESIS OF 4-AMINO-1H-PYRROLO[2,3-B]PYRIDINE (1,7-DIDEAZAADENINE) AND 1H-PYRROLO[2,3-B]PYRIDINE-4-OL (1,7-DIDEAZAHYPOXANTHINE)
    SCHNELLER, SW
    LUO, JK
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20): : 4045 - 4048
  • [46] Synthesis of 3-substituted pyrrolo[2,3-b]pyridin-2-one derivatives
    Viaud, MC
    Jamoneau, P
    Guillaumet, G
    SYNTHETIC COMMUNICATIONS, 1997, 27 (22) : 3861 - 3870
  • [47] Synthesis of 3-substituted pyrrolo[2,3-b]pyridin-2-one derivatives
    Inst. Chim. Organique Analytique, A., Université d'Orléans, B.P. 6759, 45067 Orléans Cedex 2, France
    SYNTH. COMMUN., 22 (3861-3870):
  • [48] REACTION OF 1,2-DIAMINES WITH A 2,3-DIOXOPYRROLIDINE AS AN APPROACH TO PYRROLO[2,3-B]PYRAZINES
    SCHNELLER, SW
    SUN, JH
    HETEROCYCLES, 1977, 6 (02) : 137 - 142
  • [49] PYRROLOQUINOLINES .1. SYNTHESIS OF 1-ARYL-2-CHLORO-1H-PYRROLO[2,3-B]QUINOLINES
    SHANMUGAM, P
    THIRUVENGADAM, TK
    RAMAKRISHNAN, VT
    SYNTHESIS-STUTTGART, 1976, (06): : 393 - 394
  • [50] Chemoselective asymmetric synthesis of C-3a-(3-hydroxypropyl)tetrahydropyrrolo[2,3-b]indole and C-4a-(2-aminoethyl)tetrahydropyrano[2,3-b]indole derivatives
    Pellegrino, Sara
    Clerici, Francesca
    Contini, Alessandro
    Leone, Samantha
    Pilati, Tullio
    Gelmi, Maria Luisa
    TETRAHEDRON, 2009, 65 (10) : 1995 - 2004