484-49-1Relevant academic research and scientific papers
Divergent Syntheses of Carbazole Alkaloids
Ji, Feixiang,Huang, He,Li, Mengyang,Guo, Yanqin,Song, Chuanjun,Chang, Junbiao
, p. 3921 - 3926 (2018)
Starting from common intermediate methyl 1-hydroxy-9 H -carbazole-3-carboxylate, synthetic routes toward murrayaquinone A, olivacine, and N -methylcalothrixin B were developed.
Total synthesis of ellipticine quinones, olivacine, and calothrixin b
Ramkumar, Nagarajan,Nagarajan, Rajagopal
, p. 736 - 741 (2014)
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.
Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade
Dilek, ?mer,Patir, Süleyman,Tilki, Tahir,Ertürk, Erkan
, p. 7901 - 7916 (2019/06/17)
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.
Synthesis and activity against mycobacterium tuberculosis of olivacine and oxygenated derivatives
Schmidt, Ulrike,Theumer, Gabriele,J?ger, Anne,Kataeva, Olga,Wan, Baojie,Franzblau, Scott G.,Kn?lker, Hans-Joachim
, (2018/06/15)
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.
Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6π-Electrocyclization
Itoh, Tomoki,Abe, Takumi,Choshi, Tominari,Nishiyama, Takashi,Yanada, Reiko,Ishikura, Minoru
, p. 2290 - 2299 (2016/05/19)
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.
Benzannulation of indoles to carbazoles and its applications for syntheses of carbazole alkaloids
Zheng, Xiaojian,Lv, Leiyang,Lu, Shenglin,Wang, Wenxiao,Li, Zhiping
supporting information, p. 5156 - 5159 (2014/12/11)
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.
Synthesis of 3-methoxyolivacine and olivacine by Friedel-Crafts reaction of indole-2,3-dicarboxylic anhydride with 2,4,6-trimethoxypyridine
Miki, Yasuyoshi,Tsuzaki, Yasuhiko,Hibino, Hajime,Aoki, Yoshiyuki
, p. 2206 - 2208 (2007/10/03)
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
New Synthesis of the 6H-Pyridocarbazoles Ellipticine and Olivacine via Cycloaddition of 2-Phenylsulfonyl 1,3-Dienes to Indoles
Baeckvall, Jan-E.,Plobeck, Niklas A.
, p. 4528 - 4531 (2007/10/02)
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
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
Yokoyama, Yuusaku,Okuyama, Naomi,Iwadate, Shinji,Momoi, Tokuko,Murakami, Yasuoki
, p. 1319 - 1329 (2007/10/02)
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.
THE CHEMISTRY OF THE PYRIDOCARBAZOLES PART 15. THE SYNTHESIS OF UNSYMMETRICALLY 1,4-DISUBSTITUTED CARBAZOLES AND THEIR USE IN THE SYNTHESIS OF 6H-PYRIDOCARBAZOLES
Hogan, Iain,Jenkins, Paul D.,Sainsbury, Malcolm
, p. 2943 - 2964 (2007/10/02)
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-
