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1
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0034006916
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A review of indole-containing natural products:
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A review of indole-containing natural products:. Lounasmaa M., and Tolvanen A. Nat. Prod. Rep. 17 (2000) 175-191
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(2000)
Nat. Prod. Rep.
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, pp. 175-191
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Lounasmaa, M.1
Tolvanen, A.2
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2
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62649098650
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Vinblastine and Vincristine alkaloids belong to Vinca family and they have been widely used in medicine for treating diverse types of cancer (lymphomas, sarcomas, testicular and breast cancer, leukaemia, etc.) due to their strong antineoplastic activity. See: Antitumor Bisindole Alkaloids from Catharanthus roseus (L.). Brossi A., and Suffness M. (Eds), Academic Press, New York and references cited therein
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Vinblastine and Vincristine alkaloids belong to Vinca family and they have been widely used in medicine for treating diverse types of cancer (lymphomas, sarcomas, testicular and breast cancer, leukaemia, etc.) due to their strong antineoplastic activity. See: Antitumor Bisindole Alkaloids from Catharanthus roseus (L.). In: Brossi A., and Suffness M. (Eds). The Alkaloids Vol. 37 (1990), Academic Press, New York 1-240 and references cited therein
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(1990)
The Alkaloids
, vol.37
, pp. 1-240
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3
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0001466422
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DeVita Jr. V.T., Hellman S., and Rosenberg S.A. (Eds), Lippincott-Raven, Philadelphia
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Rowinsky E.C., and Donehover R.C. In: DeVita Jr. V.T., Hellman S., and Rosenberg S.A. (Eds). Cancer Principles and Practice of Oncology. 5th ed. (1997), Lippincott-Raven, Philadelphia 467
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(1997)
Cancer Principles and Practice of Oncology. 5th ed.
, pp. 467
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Rowinsky, E.C.1
Donehover, R.C.2
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4
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33645975523
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Boussard M.-F., Truche S., Rousseau-Rojas A., Briss S., Desamps S., Droual M., Wierzbicki M., Ferry G., Audinot V., Delagrange P., and Boutin J.A. Eur. J. Med. Chem. 41 (2006) 306-320
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(2006)
Eur. J. Med. Chem.
, vol.41
, pp. 306-320
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Boussard, M.-F.1
Truche, S.2
Rousseau-Rojas, A.3
Briss, S.4
Desamps, S.5
Droual, M.6
Wierzbicki, M.7
Ferry, G.8
Audinot, V.9
Delagrange, P.10
Boutin, J.A.11
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5
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34547274208
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Only a few spattered examples of isolated indolo[1,2-a]indoles have been reported thus far, and mostly as byproducts or in low yields. See:
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Only a few spattered examples of isolated indolo[1,2-a]indoles have been reported thus far, and mostly as byproducts or in low yields. See:. Samsoniya Sh.A., and Trapaidze M.V. Russ. Chem. Rev. 76 (2007) 313-326
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(2007)
Russ. Chem. Rev.
, vol.76
, pp. 313-326
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Samsoniya, Sh.A.1
Trapaidze, M.V.2
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13
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0034704888
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Faust R., Garratt P.J., Jones R., Yeh L.-K., Tsotinis A., Panoussopoulou M., Calogeropoulou T., The M.-T., and Sugden D. J. Med. Chem. 43 (2000) 1050-1061
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(2000)
J. Med. Chem.
, vol.43
, pp. 1050-1061
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Faust, R.1
Garratt, P.J.2
Jones, R.3
Yeh, L.-K.4
Tsotinis, A.5
Panoussopoulou, M.6
Calogeropoulou, T.7
The, M.-T.8
Sugden, D.9
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14
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0010372638
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The intramolecular direct arylation of indole with aryl iodides through a palladium-catalysed process was first reported by Grigg and co-workers. See:
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The intramolecular direct arylation of indole with aryl iodides through a palladium-catalysed process was first reported by Grigg and co-workers. See:. Grigg R., Sridharan V., Stevenson P., Sukirthalingam S., and Worakun T. Tetrahedron 46 (1990) 4003-4018
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(1990)
Tetrahedron
, vol.46
, pp. 4003-4018
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Grigg, R.1
Sridharan, V.2
Stevenson, P.3
Sukirthalingam, S.4
Worakun, T.5
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15
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31544455027
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Recently, Fagnou et al. published the preparation of isoindolo[2,1-a]indole 1 through an intramolecular palladium-catalysed direct arylation of an aryl chloride. See:
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Recently, Fagnou et al. published the preparation of isoindolo[2,1-a]indole 1 through an intramolecular palladium-catalysed direct arylation of an aryl chloride. See:. Campeau L.-C., Parisien M., Jean A., Fagnou K. J. Am. Chem. Soc. 128 (2006) 581-590
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(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 581-590
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Campeau, L.-C.1
Parisien, M.2
Jean, A.3
Fagnou, K.4
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17
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18844405201
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A palladium-catalysed indole alkenylation by C-H functionalisation aided by copper oxidants is reported in:
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A palladium-catalysed indole alkenylation by C-H functionalisation aided by copper oxidants is reported in:. Grimser N.P., Gaunlett C., Godfrey C.R.A., and Gaunt M.J. Angew. Chem., Int. Ed. 44 (2005) 3125-3129
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(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 3125-3129
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Grimser, N.P.1
Gaunlett, C.2
Godfrey, C.R.A.3
Gaunt, M.J.4
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21
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42949170450
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Recently, an iron-catalysed direct arylation of α-benzoquinolines has been reported. See:
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Recently, an iron-catalysed direct arylation of α-benzoquinolines has been reported. See:. Norinder J., Matsumoto A., Yoshikai N., and Nakamura E. J. Am. Chem. Soc. 130 (2008) 5858-5859
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(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 5858-5859
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Norinder, J.1
Matsumoto, A.2
Yoshikai, N.3
Nakamura, E.4
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22
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2442685496
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He et al. reported a gold-catalysed functionalisation of aromatic C-H bonds. See:
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He et al. reported a gold-catalysed functionalisation of aromatic C-H bonds. See:. Shi Z., He C. J. Org. Chem. 69 (2004) 3669-3671
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(2004)
J. Org. Chem.
, vol.69
, pp. 3669-3671
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Shi, Z.1
He, C.2
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25
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47749142816
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For a review on catalytic C-C, C-N and C-O Ullmann-type coupling reactions, see:
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For a review on catalytic C-C, C-N and C-O Ullmann-type coupling reactions, see:. Monnier F., and Taillefer M. Angew. Chem., Int. Ed. 47 (2008) 3096-3099
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(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 3096-3099
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Monnier, F.1
Taillefer, M.2
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29
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54049087464
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2 (1.0 equiv) has been used for non-selective, multiple C-H bond arylation of indoles and pyrroles. See:
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2 (1.0 equiv) has been used for non-selective, multiple C-H bond arylation of indoles and pyrroles. See:. Ban I., Sudo T., Taniguchi T., and Itami K. Org. Lett. 10 (2008) 3607-3609
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(2008)
Org. Lett.
, vol.10
, pp. 3607-3609
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Ban, I.1
Sudo, T.2
Taniguchi, T.3
Itami, K.4
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30
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53049104239
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and references cited therein
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Borduas N., and Powell D.A. J. Org. Chem. 73 (2008) 7822-7825 and references cited therein
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(2008)
J. Org. Chem.
, vol.73
, pp. 7822-7825
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Borduas, N.1
Powell, D.A.2
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34
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4143104684
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Only N-arylation of unprotected indoles has been achieved thus far, as reported by Buchwald. See:
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Only N-arylation of unprotected indoles has been achieved thus far, as reported by Buchwald. See:. Antilla J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578-5587
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(2004)
J. Org. Chem.
, vol.69
, pp. 5578-5587
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Antilla, J.C.1
Baskin, J.M.2
Barder, T.E.3
Buchwald, S.L.4
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35
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46049110936
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A direct, elegant arylation of indoles using diaryl-iodine(III) reagents can be found in:
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A direct, elegant arylation of indoles using diaryl-iodine(III) reagents can be found in:. Phipps R.J., Grimster N.P., and Gaunt M.J. J. Am. Chem. Soc. 130 (2008) 8172-8174
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(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 8172-8174
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Phipps, R.J.1
Grimster, N.P.2
Gaunt, M.J.3
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38
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40849119590
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The use of PEG as additive and/or solvent in copper-catalysed reactions has been reported. See:
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The use of PEG as additive and/or solvent in copper-catalysed reactions has been reported. See:. Mao J., Guo J., Fang F., and Ji S.-J. Tetrahedron 64 (2008) 3905-3911
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(2008)
Tetrahedron
, vol.64
, pp. 3905-3911
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Mao, J.1
Guo, J.2
Fang, F.3
Ji, S.-J.4
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44
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33645910529
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Apparently, the aliphatic diamine could play both the role of base and ligand. See:
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Apparently, the aliphatic diamine could play both the role of base and ligand. See:. Carril M., SanMartin R., Tellitu M., and Domínguez E. Org. Lett. 8 (2006) 1467-1470
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(2006)
Org. Lett.
, vol.8
, pp. 1467-1470
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Carril, M.1
SanMartin, R.2
Tellitu, M.3
Domínguez, E.4
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45
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0034794463
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These conditions had proved successful for the N-arylation of some nitrogen-containing heterocycles. See:
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These conditions had proved successful for the N-arylation of some nitrogen-containing heterocycles. See:. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
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(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7727-7729
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Klapars, A.1
Antilla, J.C.2
Huang, X.3
Buchwald, S.L.4
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62649093409
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note
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4 and concentrated in vacuo. The resulting residue was purified by flash chromatography (10% AcOEt/n-hexane) to afford the target tetracyclic product 1 as a white powder (52.3 mg, 88%). The physical data were compared with those found in the literature. See: Ref. 9c.
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47
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62649107779
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note
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4 and concentrated in vacuo. The resulting residue was purified by flash chromatography (10% AcOEt/n-hexane) to afford the target tetracyclic product 2 as a white powder (51.0 mg, 88%). For physical data see Supplementary data.
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