4241-44-5Relevant academic research and scientific papers
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.
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.
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
