- Divergent Syntheses of Carbazole Alkaloids
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Starting from common intermediate methyl 1-hydroxy-9 H -carbazole-3-carboxylate, synthetic routes toward murrayaquinone A, olivacine, and N -methylcalothrixin B were developed.
- Ji, Feixiang,Huang, He,Li, Mengyang,Guo, Yanqin,Song, Chuanjun,Chang, Junbiao
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- Total synthesis of ellipticine quinones, olivacine, and calothrixin b
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A direct route to the synthesis of biologically active ellipticine quinones, olivacine, and calothrixin B is described. The prominent key steps involved are Friedel-Crafts hydroxyalkylation followed by oxidation and directed ortho-lithiation reactions of readily available indole-2-carboxylate esters with appropriately substituted pyridine and quinoline carboxaldehydes.
- Ramkumar, Nagarajan,Nagarajan, Rajagopal
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- Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade
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Effective preparation of olivacine and ellipticine via late-stage D-ring cyclization is described. Key features of the synthetic routes include trifluoroacetic acid-mediated formation of a lactone that is fused to a tetrahydrocarbazole derivative and its one-pot two-step ring opening and aromatization mediated by para-toluenesulfonic acid and palladium on carbon, respectively.
- Dilek, ?mer,Patir, Süleyman,Tilki, Tahir,Ertürk, Erkan
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p. 7901 - 7916
(2019/06/17)
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- Synthesis and activity against mycobacterium tuberculosis of olivacine and oxygenated derivatives
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The tetracyclic pyrido[4,3-b]carbazole olivacine and four of its oxygenated derivatives have been synthesized by a late-stage palladium-catalyzed Heck-type cyclization of the pyrrole ring as a key step. In a test for the inhibition of the growth of Mycobacterium tuberculosis, 9-methoxyolivacine showed the most significant inhibitory activity against Mycobacterium tuberculosis, with an MIC90 value of 1.5 μM.
- Schmidt, Ulrike,Theumer, Gabriele,J?ger, Anne,Kataeva, Olga,Wan, Baojie,Franzblau, Scott G.,Kn?lker, Hans-Joachim
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- Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6π-Electrocyclization
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Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (μ-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (±)-guatambuine, and (±)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6π-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids. Concise total syntheses of pyrido[4,3-b]carbazole alkaloids were accomplished using Cu-catalyzed 6π-electrocyclization of hexatriene as a key step.
- Itoh, Tomoki,Abe, Takumi,Choshi, Tominari,Nishiyama, Takashi,Yanada, Reiko,Ishikura, Minoru
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p. 2290 - 2299
(2016/05/19)
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- Benzannulation of indoles to carbazoles and its applications for syntheses of carbazole alkaloids
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A novel and efficient method for the benzannulation of indoles to carbazoles is reported. γ-Carbonyl tert-butylperoxide is applied as a new diene building block for the π-extension of simple indoles. The synthetic utility of this method is demonstrated by concise and selective total syntheses of naturally occurring carbazole alkaloids, olivacine, and asteropusazole A.
- Zheng, Xiaojian,Lv, Leiyang,Lu, Shenglin,Wang, Wenxiao,Li, Zhiping
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p. 5156 - 5159
(2014/12/11)
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- Synthesis of 3-methoxyolivacine and olivacine by Friedel-Crafts reaction of indole-2,3-dicarboxylic anhydride with 2,4,6-trimethoxypyridine
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1-Benzylindole-2,3-dicarboxylic anhydride (1) was reacted with 2,4,6-trimethoxypyridine in the presence of titanium(IV) chloride to give 3-(2,4,6-trimethoxynicotinoyl)indole-2-carboxylic acid (2) as the sole product in high yield, which could be converted
- Miki, Yasuyoshi,Tsuzaki, Yasuhiko,Hibino, Hajime,Aoki, Yoshiyuki
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p. 2206 - 2208
(2007/10/03)
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- New Synthesis of the 6H-Pyridocarbazoles Ellipticine and Olivacine via Cycloaddition of 2-Phenylsulfonyl 1,3-Dienes to Indoles
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An efficient synthesis of the antitumor alkaloids ellipticine and olivacine, starting from indole, was developed.The cycloaddition of 3-(phenylsulfonyl)-2,4-hexadiene or 2-(phenylsulfonyl)-1,3-pentadiene to the magnesium salt of indole was followed by C-C
- Baeckvall, Jan-E.,Plobeck, Niklas A.
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p. 4528 - 4531
(2007/10/02)
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- THE CHEMISTRY OF THE PYRIDOCARBAZOLES PART 15. THE SYNTHESIS OF UNSYMMETRICALLY 1,4-DISUBSTITUTED CARBAZOLES AND THEIR USE IN THE SYNTHESIS OF 6H-PYRIDOCARBAZOLES
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A new construction of unsymmetrically 1,4-disubstituted carbazoles has been devised and used in the synthesis of the alkaloid olivacine.The starting materials are gramines and the sodium salts of 2-cyano-4-oxopentanonitriles.These afford 4-cyano-5-(indol-
- Hogan, Iain,Jenkins, Paul D.,Sainsbury, Malcolm
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p. 2943 - 2964
(2007/10/02)
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- Synthetic Studies of Indoles and Related Compounds, Part 221. The Vilsmeier-Haack Reaction of N-Benzyl-1,2,3,4-tetrahydrocarbazoles and its Synthetic Application to Olivacine and Ellipticine2
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Vilsmeier-Haack reaction of 9-benzyl-1,2,3,4-tetrahydrocarbazole (18a) at 120 deg C gave 9-benzyl-1-methylcarbazole-3-carbaldehyde (19a) and 9-benzyl-1-(N,N-(dimethylamino)methyl)carbazole-3-carbaldehyde (22a) in moderate yields, whereas, the same reaction at 0 deg C gave 9-benzyl-1,2,3,4-tetrahydrocarbazole-1-carbaldehyde (20a) in very good yield.The aldehyde (20a) was converted into 9-benzyl-1-methylcarbazole (21a) by another Vilsmeier-Haack reaction.This carbazole (21a) unexpectedly underwent non-regioselective formylation under similar reaction conditions to give a mixture of compound (19a) and 9-benzyl-8-methylcarbazole-3-carbaldehyde (23a).On the basis of the above results, a mechanism of the formation of the aromatic aldehyde (19a) was proposed, which involves 1,5-sigmatropic rearrangement of an N-methylidene dimethylammonium cation from the 4a-position to the 3-position as a key step.Vilsmeier-Haack reaction of 9-benzyl-1,2,3,4-tetrahydro-4-methylcarbazole (18b) at 100 deg C also gave 9-benzyl-1,4-dimethylcarbazole-3-carbaldehyde (19b) in moderate yield.The total syntheses of two antitumor alkaloids, olivacine (10) and ellipticine (11), were achieved by utilizing compounds (19a) and (19b) as key intermediates.
- Yokoyama, Yuusaku,Okuyama, Naomi,Iwadate, Shinji,Momoi, Tokuko,Murakami, Yasuoki
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p. 1319 - 1329
(2007/10/02)
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- AN EFFICIENT SYNTHESYS OF 3-ACYLCARBAZOLES AND OBSERVATIONS ON THE FURTHER ELABORATION OF THESE COMPOUNDS TO 6H-PYRIDOCARBAZOLES
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A new procedure for the synthesis of 3-acylcarbazoles useful for the construction of 6H-pyridocarbazoles is described starting from readily available gramines or indoles.This methodology is exemplified by a synthesis of the anticancer alkaloid olivacine.Some discrepancies are noted between our results and those of other authors.
- Hogan, Iain,Jenkins, Paul,Sainsbury, Malcolm
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p. 6505 - 6508
(2007/10/02)
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- New Synthesis of Olivacine via Heteroarylation
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Heteroarylation under acylating conditions, between indole and 4-substituted pyridines (1a-c), followed by acidic cyclisation, provides a useful route to indole alkaloids, as exemplified by a new synthesis of olivacine (12).
- Naito, Takeaki,Iida, Naoko,Ninomiya, Ichiya
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- THE VILSMEIER-HAACK REACTION OF N-ALKYL-1,2,3,4-TETRAHYDROCARBAZOLES AND THE SYNTHETIC APPLICATION TO OLIVACINE AND ELLIPTICINE
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The mechanism of the formation of products resulting from the Vilsmeier-Haack reaction of N-alkyl-1,2,3,4-tetrahydrocarbazoles, and the synthetic application to olivacine and ellipticine, are described.
- Murakami, Yasuoki,Yokoyama, Yuusaku,Okuyama, Naomi
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p. 2189 - 2192
(2007/10/02)
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- A NEW SYNTHESIS OF ELLIPTICINE AND OLIVACINE THROUGH PYRIDINE-3,4-QUINODIMETHANE INTERMEDIATES
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Thermolysis of 2-indole (6a) at 500 deg C for 3 min gave 11-demethylellipticine (7a).The similar reaction by using 2-indole (6b) affordedolivacine (7b).Ellipticine and 11-demethylellipticine were obtained by thermolysis of 2-indole (6c).
- Kano, Shinzo,Sugino, Eiichi,Hibino, Satoshi
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p. 1673 - 1676
(2007/10/02)
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- STUDIES IN THE DIHYDROPYRIDINE SERIES. V. SYNTHESIS OF PYRIDOCARBAZOLE ALKALOIDS: OLIVACINE AND GUATAMBUINE.
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The tricarbonylchromium(0) complex 8 effectively stabilized the very reactive dihydropyridine system during one carbon insertion.Release of the complex allowed cyclization to the pyridocarbazole product 13 which was elaborated to olivacine 1 and guatambuine 2.
- Kutney, James P.,Noda, Masaki,Lewis, Norman G.,Monteiro, Beatrice,Mostowicz, Danuta,Worth, Brian R.
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p. 1469 - 1472
(2007/10/02)
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- New Synthesis of Olivacine via a Heteroarylation Reaction
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The heteroarylation reaction between indole and 4-substituted pyridines under acylating conditions, followed by acidic cyclisation, provides a useful route to indole alkaloides, as exemplified by a new synthesis of olivacine.
- Naito, T.,Iida, N.,Ninomiya, I.
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