.. Analyse-de-rétrosynthèse, 48 III.5.2) 9H-Carbazole et 2,3,4,9-tétrahydro-1H-carbazole en tant que produits de départ, p.49

.. Synthèses-indoliques-de-fischer, 50 III.5.3)a) Généralités sur la synthèse indolique de, p.51

V. 1. Introduction and .. , 107 V.3. ESSAI A PARTIR DE LA 5, 107 V.2. ESSAI AU DEPART DU 2, pp.8-11

C. Vi:-partie-experimentale-2 and .. , 118 VI.1. Synthèse du 2-cyclohexylidènemalononitrile 93 118 VI.2. Synthèse de la 3-chloro-4 119 VI.3. Synthèse de la 3-chloro-4-carboxamide-5 121 VI.5. Synthèse du 2-cyclohexylidènecyanoacétate de méthyle 98, -tétrahydroisoquinoléine 94 ... 120 VI.4. Synthèse du 2-cyclohexylidènecyanoacétate d'éthyle 97, p.132, 1992.

V. 2. Synthese-d-'analogues and .. De-l-'ellipticine, 136 VII.3, 139 VII.3.2) Nouvelle synthèse du, pp.12-12

C. Viii:-partie-experimentale-3 and .. , 147 VIII.2. Synthèse du 6-chloro-12-méthyl-1 149 VIII.3. Synthèse de la N 1 ,N 1 -diéthyl-N 3 -(12-méthyl-1,2,3,12-tétrahydroisoquino[5,4- ab]carbazol-6-yl)-1,3-propanediamine 112 150 VIII.4. Méthode générale pour la synthèse des 5, ., vol.5235672131, pp.12-12

B. Dans-les-synthèses-de-type, isoquinoléine (cycles C et D) diversement substitué est d'abord synthétisé puis la synthèse du cycle indolique se fait : 29, 30, 31, 32 -par synthèse indolique de Fischer 29-32 -par cyclisation thermique de nitrènes 33, pp.34-35

B. S. Archer, L. Ross, D. Pica-mattoccia, and . Cioli, Synthesis and biological properties of some 6H-pyrido[4,3-b]carbazoles, Journal of Medicinal Chemistry, vol.30, issue.7, p.1204, 1987.
DOI : 10.1021/jm00390a014

B. Miller and J. G. Stowell, Total synthesis of ellipticine and 9-methoxyellipticine via benzotriazole intermediates, The Journal of Organic Chemistry, vol.48, issue.6, p.886, 1983.
DOI : 10.1021/jo00154a030

L. Goffic, A. Gouyette, and A. Ahond, Une nouvelle synthese de l'ellipticine et ses analogues structuraux, Tetrahedron, vol.29, issue.21, p.3357, 1973.
DOI : 10.1016/S0040-4020(01)93489-1

Y. Kametani, T. Ichikawa, K. Suzuki, and . Fukumoto, A Fascinating Synthesis of Olivacine, HETEROCYCLES, vol.3, issue.5, p.401, 1975.
DOI : 10.3987/R-1975-05-0401

P. Kozikowski and N. M. Hasan, Oxazoles in organic chemistry. Synthesis of the antitumor agent ellipticine, The Journal of Organic Chemistry, vol.42, issue.11, p.2039, 1977.
DOI : 10.1021/jo00431a059

V. Watanabe and . Snieckus, Tandem directed metalation reactions. Short syntheses of polycyclic aromatic hydrocarbons and ellipticine alkaloids, Journal of the American Chemical Society, vol.102, issue.4, p.1457, 1980.
DOI : 10.1021/ja00524a059

G. Saulnier and G. W. Gribble, An efficient synthesis of ellipticine, The Journal of Organic Chemistry, vol.47, issue.14, p.2810, 1982.
DOI : 10.1021/jo00135a034

J. Wanner, G. Koomen, and U. K. Pandit, Inter- and intramolecular addition of ester anions to nicotinium salts, Tetrahedron, vol.39, issue.22, p.3673, 1983.
DOI : 10.1016/S0040-4020(01)88606-3

M. Ketcha and G. W. Gribble, A convenient synthesis of 3-acylindoles via Friedel Crafts acylation of 1-(phenylsulfonyl)indole. A new route to pyridocarbazole-5,11-quinones and ellipticine, The Journal of Organic Chemistry, vol.50, issue.26, p.5451, 1985.
DOI : 10.1021/jo00350a001

A. Obaza-nutaitis and G. W. Gribble, Synthesis of 13-Oxoellipticine, Journal of Natural Products, vol.49, issue.3, p.449, 1986.
DOI : 10.1021/np50045a011

M. Bisagni, C. Rautureau, and . Huel, 1-Functionalized 5,6-Dimethyl-6H-pyrido[4,3-b]carbazoles (Ellipticines) and Analogues: A New Rapid Synthesis, HETEROCYCLES, vol.27, issue.7, p.1671, 1988.
DOI : 10.3987/COM-88-4543

P. Modi, T. Mccomb, A. Zayed, R. C. Oglesby, and S. Archer, Synthesis of 6h-pyrido[4,3-b]carbazoles, Tetrahedron, vol.46, issue.16, p.5555, 1990.
DOI : 10.1016/S0040-4020(01)87753-X

C. Ruckdeschel, S. P. Modi, W. El-hamouly, E. Portuese, and S. Archer, N-Methylcarbamate derivatives of ellipticine and olivacine with cytotoxic activity against four human lung cancer cell lines, Journal of Medicinal Chemistry, vol.35, issue.26, p.4854, 1992.
DOI : 10.1021/jm00104a011

W. Gribble, M. G. Saulnier, J. A. Obaza-nutaitis, and D. M. Ketcha, A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs, The Journal of Organic Chemistry, vol.57, issue.22, p.5891, 1992.
DOI : 10.1021/jo00048a022

J. Dormoy and A. Heymes, Synthese industrielle en serie ellipticine. I, Tetrahedron, vol.49, issue.14, p.2885, 1993.
DOI : 10.1016/S0040-4020(01)80387-2

J. Dormoy and A. Heymes, Synthese industrielle en serie ellipticine. II, Tetrahedron, vol.49, issue.14, p.2915, 1993.
DOI : 10.1016/S0040-4020(01)80388-4

T. Boogaard, U. K. Pandit, and G. Koomen, Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole., Tetrahedron, vol.50, issue.16, p.4811, 1994.
DOI : 10.1016/S0040-4020(01)85018-3

Y. Miki, K. Tada, and . Matsushita, Reaction of 1-Benzylindole-2,3-dicarboxylic Anhydride with 3-Bromo-4-lithiopyridine: Formal Synthesis of Ellipticine, HETEROCYCLES, vol.48, issue.8, p.1593, 1998.
DOI : 10.3987/COM-98-8192

Y. Miki, Y. Aoki, M. Tsuzaki, H. Umemoto, and . Hibino, Synthesis of 3-Methoxyellipticine and Ellipticine by Friedel-Crafts Reaction of Indole-2,3-dicarboxylic Anhydride and Selective Demethylation, HETEROCYCLES, vol.65, issue.11, p.2693, 2005.
DOI : 10.3987/COM-05-10522

E. Kano, S. Sugino, S. Shibuya, and . Hibino, New synthesis of the antitumor 6H-pyrido[4,3-b]carbazole alkaloid ellipticine, The Journal of Organic Chemistry, vol.46, issue.14, p.2979, 1981.
DOI : 10.1021/jo00327a031

E. Kano, S. Sugino, and . Hibino, A New Synthesis of Ellipticine and Olivacine through Pyridine-3,4-quinodimethane Intermediates, HETEROCYCLES, vol.19, issue.9, p.1673, 1982.
DOI : 10.3987/R-1982-09-1673

E. Hibino and . Sugino, pyridine 3,4-quinodimethane intermediates, Journal of Heterocyclic Chemistry, vol.45, issue.6, p.1751, 1990.
DOI : 10.1248/cpb.7.930

A. Ishikura, N. Hino, and . Katagiri, An Efficient Total Synthesis of Ellipticine, HETEROCYCLES, vol.53, issue.1, p.11, 2000.
DOI : 10.3987/COM-99-8759

A. Ishikura, T. Hino, I. Yaginuma, N. Agata, and . Katagiri, A Novel Entry to Pyrido[4,3-b]carbazoles: An Efficient Synthesis of Ellipticine, Tetrahedron, vol.56, issue.2, p.193, 2000.
DOI : 10.1016/S0040-4020(99)01016-9

M. Bennasar, T. Roca, and F. Ferrando, Regioselective Intramolecular Reactions of 2-Indolylacyl Radicals with Pyridines:?? A Direct Synthetic Entry to Ellipticine Quinones, The Journal of Organic Chemistry, vol.70, issue.22, p.9077, 2005.
DOI : 10.1021/jo0514974

W. Gribble, M. G. Saulnier, M. P. Sibi, and J. A. Obaza-nutaitis, Synthesis and Diels-Alder reactions of 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. A new annulation strategy for the construction of ellipticine and isoellipticine, The Journal of Organic Chemistry, vol.49, issue.23, p.4518, 1984.
DOI : 10.1021/jo00197a039

C. Sha and J. Yang, Total syntheses of ellipticine alkaloids and their amino analogues, Tetrahedron, vol.48, issue.48, p.10645, 1992.
DOI : 10.1016/S0040-4020(01)88360-5

K. Haider, R. Mereiter, and . Wanko, [4+2]Cycloaddition Reactions of 1,4-Bis(trifluoromethyl)pyrido[3,4-d]pyridazine with Indole-Type Dienophiles, HETEROCYCLES, vol.41, issue.7, p.1445, 1995.
DOI : 10.3987/COM-95-7063

K. Dalton, S. Demerac, B. C. Elmes, J. W. Loder, J. M. Swan et al., Synthesis of the tumour-inhibitory alkaloids, ellipticine, 9-methoxyellipticine, and related pyrido[4,3-b]carbazoles, Australian Journal of Chemistry, vol.20, issue.12, p.2715, 1967.
DOI : 10.1071/CH9672715

W. Guthrie, A. Brossi, F. A. Mennona, J. G. Mullin, and R. W. Kierstead, Ellipticine derivatives, Journal of Medicinal Chemistry, vol.18, issue.7, p.755, 1975.
DOI : 10.1021/jm00241a023

I. Hogan and P. D. Jenkins, The chemistry of the pyrido[4,3-b]carbazoles part 15 the synthesis of unsymmetrically 1,4-disubstituted carbazoles and their use in the synthesis of 6H-Pyrido-[4,3-b]carbazoles, Tetrahedron, vol.46, issue.8, p.2943, 1990.
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. Archer, 32 (type B, synthèse indolique de Fischer

Y. Ergün, S. Patir, and G. Okay, Total synthesis of 5-demethylellipticine, Journal of Heterocyclic Chemistry, vol.24, issue.6, p.1445, 1998.
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Y. Ergün, S. Patir, and G. Okay, A Novel Synthesis Towards Ellipticine and Its Derivatives. Synthesis of a New Precursor Compound, Synthetic Communications, vol.1, issue.3, p.435, 2004.
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P. Kutney and D. S. Grierson, An Improved Synthesis of the Pyridocarbazole Indole Alkaloid Olivacine, HETEROCYCLES, vol.3, issue.2, p.171, 1975.
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M. Oikawa, H. Tanaka, O. Hirasawa, and . Yonemitsu, Reactions and synthetic applications of .BETA.-keto sulfoxides. X. Synthesis of ellipticine analogs modified at the 5-position., CHEMICAL & PHARMACEUTICAL BULLETIN, vol.29, issue.6, p.1606, 1981.
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J. Bäckvall and N. A. Plobeck, New synthesis of the 6H-pyrido[4,3-b]carbazoles ellipticine and olivacine via cycloaddition of 2-phenylsulfonyl 1,3-dienes to indoles, The Journal of Organic Chemistry, vol.55, issue.15, p.4528, 1990.
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H. Besselièvre, T. Husson, and . Lett, 1873 -1971 : intercalation entre les paires de bases de l'ADN 156 -1981 et 1983 : bioactivation et formation d'espèces réactives alkylantes 157, 158 -1982 : inhibition de la topoisomérase II, pp.159-2005, 1976.

. Ainsi, la manière dont un dérivé d'ellipticine précis agit pour donner son effet antitumoral n'est pas connue avec précision

A. Noter-que-le, Figure 5) est plus actif que l'ellipticine elle-même 163 et que l'acétate de son dérivé quaternisé par un groupement méthyle sur la position 1 (céliptium 16, Figure 5) a été utilisé jadis comme médicament anticancéreux, pp.162-171

. Après-la-vue-d, ensemble sur les synthèses d'ellipticines, voyons à présent ce qui a initié notre projet. Il s'agit plus particulièrement des recherches du groupe de Bisagni qui a travaillé intensément sur le sujet de, 1975.

. Depuis-le-céliptium, méthyl-9-hydroxyellipticinium) 16 développé par Le Pecq et coll., 164, 165 utilisé comme médicament en France dans les années plusieurs autres molécules (18 à 20 Figure 5) synthétisées par l'équipe de Bisagni ont révélé d'importantes 156, FEBS Letters, vol.166, issue.17, pp.167-321, 1971.

C. Auclair and C. Paoletti, Bioactivation of the antitumor drugs 9-hydroxyellipticine and derivatives by a peroxidase-hydrogen peroxide system, Journal of Medicinal Chemistry, vol.24, issue.3, p.289, 1981.
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J. Bernardou, G. Meunier, C. Paoletti, and B. Meunier, o-Quinone formation in the biochemical oxidation of the antitumor drug N2-methyl-9-hydroxyellipticinium acetate, Journal of Medicinal Chemistry, vol.26, issue.4, p.574, 1983.
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A. Juret, A. Tanguy, J. Y. Girard, J. S. Le-talaer, N. D. Abbatucci et al., Preliminary trial of 9-hydroxy-2-methyl ellipticinium (NSC 264-137) in advanced human cancers, European Journal of Cancer (1965), vol.14, issue.2, p.205, 1978.
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. Masse, 40 mg Rendement : 85% Aspect : solide jaune pâle R f : 0

. Masse, 01 g Rendement : 4% Aspect : solide rose pâle R f : 0

. Masse, 0 g Rendement : 52% Aspect : solide marron R f : 0

. Masse, 70 mg Rendement : 51% Aspect : solide rose pâle R f : 0, p.45

T. Ms, 141 (calculée : 306,116) N H HN VIII.8. Synthèse du 13-méthyl-12,13-dihydro-7H-indolo[2',3':3,4]cyclopenta[1,2-a]carbazole REFERENCES BIBLIOGRAPHIQUES F. Wöhler, Ann. Phys. Chem, vol.306, issue.12, p.253

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L. Goffic, A. Gouyette, and A. Ahond, Une nouvelle synthese de l'ellipticine et ses analogues structuraux, Tetrahedron, vol.29, issue.21, p.3357, 1973.
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Y. Kametani, T. Ichikawa, K. Suzuki, and . Fukumoto, A Fascinating Synthesis of Olivacine, HETEROCYCLES, vol.3, issue.5, p.401, 1975.
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P. Kozikowski and N. M. Hasan, Oxazoles in organic chemistry. Synthesis of the antitumor agent ellipticine, The Journal of Organic Chemistry, vol.42, issue.11, p.2039, 1977.
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V. Watanabe and . Snieckus, Tandem directed metalation reactions. Short syntheses of polycyclic aromatic hydrocarbons and ellipticine alkaloids, Journal of the American Chemical Society, vol.102, issue.4, p.1457, 1980.
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G. Saulnier and G. W. Gribble, An efficient synthesis of ellipticine, The Journal of Organic Chemistry, vol.47, issue.14, p.2810, 1982.
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J. Wanner, G. Koomen, and U. K. Pandit, Inter- and intramolecular addition of ester anions to nicotinium salts, Tetrahedron, vol.39, issue.22, p.3673, 1983.
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M. Ketcha and G. W. Gribble, A convenient synthesis of 3-acylindoles via Friedel Crafts acylation of 1-(phenylsulfonyl)indole. A new route to pyridocarbazole-5,11-quinones and ellipticine, The Journal of Organic Chemistry, vol.50, issue.26, p.5451, 1985.
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A. Obaza-nutaitis and G. W. Gribble, Synthesis of 13-Oxoellipticine, Journal of Natural Products, vol.49, issue.3, p.449, 1986.
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M. Bisagni, C. Rautureau, and . Huel, 1-Functionalized 5,6-Dimethyl-6H-pyrido[4,3-b]carbazoles (Ellipticines) and Analogues: A New Rapid Synthesis, HETEROCYCLES, vol.27, issue.7, p.1671, 1988.
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P. Modi, T. Mccomb, A. Zayed, R. C. Oglesby, and S. Archer, Synthesis of 6h-pyrido[4,3-b]carbazoles, Tetrahedron, vol.46, issue.16, p.5555, 1990.
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C. Ruckdeschel, S. P. Modi, W. El-hamouly, E. Portuese, and S. Archer, N-Methylcarbamate derivatives of ellipticine and olivacine with cytotoxic activity against four human lung cancer cell lines, Journal of Medicinal Chemistry, vol.35, issue.26, p.4854, 1992.
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W. Gribble, M. G. Saulnier, J. A. Obaza-nutaitis, and D. M. Ketcha, A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs, The Journal of Organic Chemistry, vol.57, issue.22, p.5891, 1992.
DOI : 10.1021/jo00048a022

J. Dormoy and A. Heymes, Synthese industrielle en serie ellipticine. I, Tetrahedron, vol.49, issue.14, p.2885, 1993.
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J. Dormoy and A. Heymes, Synthese industrielle en serie ellipticine. II, Tetrahedron, vol.49, issue.14, p.2915, 1993.
DOI : 10.1016/S0040-4020(01)80388-4

T. Boogaard, U. K. Pandit, and G. Koomen, Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole., Tetrahedron, vol.50, issue.16, p.4811, 1994.
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Y. Miki, K. Tada, and . Matsushita, Reaction of 1-Benzylindole-2,3-dicarboxylic Anhydride with 3-Bromo-4-lithiopyridine: Formal Synthesis of Ellipticine, HETEROCYCLES, vol.48, issue.8, p.1593, 1998.
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Y. Miki, Y. Aoki, M. Tsuzaki, H. Umemoto, and . Hibino, Synthesis of 3-Methoxyellipticine and Ellipticine by Friedel-Crafts Reaction of Indole-2,3-dicarboxylic Anhydride and Selective Demethylation, HETEROCYCLES, vol.65, issue.11, p.2693, 2005.
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E. Kano, S. Sugino, S. Shibuya, and . Hibino, New synthesis of the antitumor 6H-pyrido[4,3-b]carbazole alkaloid ellipticine, The Journal of Organic Chemistry, vol.46, issue.14, p.2979, 1981.
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E. Kano, S. Sugino, and . Hibino, A New Synthesis of Ellipticine and Olivacine through Pyridine-3,4-quinodimethane Intermediates, HETEROCYCLES, vol.19, issue.9, p.1673, 1982.
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E. Hibino and . Sugino, pyridine 3,4-quinodimethane intermediates, Journal of Heterocyclic Chemistry, vol.45, issue.6, p.1751, 1990.
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A. Ishikura, N. Hino, and . Katagiri, An Efficient Total Synthesis of Ellipticine, HETEROCYCLES, vol.53, issue.1, p.11, 2000.
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A. Ishikura, T. Hino, I. Yaginuma, N. Agata, and . Katagiri, A Novel Entry to Pyrido[4,3-b]carbazoles: An Efficient Synthesis of Ellipticine, Tetrahedron, vol.56, issue.2, p.193, 2000.
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M. Bennasar, T. Roca, and F. Ferrando, Regioselective Intramolecular Reactions of 2-Indolylacyl Radicals with Pyridines:?? A Direct Synthetic Entry to Ellipticine Quinones, The Journal of Organic Chemistry, vol.70, issue.22, p.9077, 2005.
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W. Gribble, M. G. Saulnier, M. P. Sibi, and J. A. Obaza-nutaitis, Synthesis and Diels-Alder reactions of 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. A new annulation strategy for the construction of ellipticine and isoellipticine, The Journal of Organic Chemistry, vol.49, issue.23, p.4518, 1984.
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C. Sha and J. Yang, Total syntheses of ellipticine alkaloids and their amino analogues, Tetrahedron, vol.48, issue.48, p.10645, 1992.
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K. Haider, R. Mereiter, and . Wanko, [4+2]Cycloaddition Reactions of 1,4-Bis(trifluoromethyl)pyrido[3,4-d]pyridazine with Indole-Type Dienophiles, HETEROCYCLES, vol.41, issue.7, p.1445, 1995.
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K. Dalton, S. Demerac, B. C. Elmes, J. W. Loder, J. M. Swan et al., Synthesis of the tumour-inhibitory alkaloids, ellipticine, 9-methoxyellipticine, and related pyrido[4,3-b]carbazoles, Australian Journal of Chemistry, vol.20, issue.12, p.2715, 1967.
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W. Guthrie, A. Brossi, F. A. Mennona, J. G. Mullin, and R. W. Kierstead, Ellipticine derivatives, Journal of Medicinal Chemistry, vol.18, issue.7, p.755, 1975.
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