13799-49-0Relevant academic research and scientific papers
A Concise Synthesis of the Antitumour Alkaloid Ellipticine
May, Christopher,Moody, Christopher J.
, p. 926 - 927 (1984)
A short synthesis of the antitumour alkaloid ellipticine, based on the Diels-Alder reaction between 1,4-dimethylpyranoindol-3-one (2) and 3,4-didehydropyridine, is described.
Synthesis and cytotoxicity of novel bisellipticines and bisisoellipticines
Obaza-Nutaitis, Judy A.,Gribble, Gordon W.
, p. 171 - 187 (2019/07/31)
A series of bis-ellipticines 7-9 and bis-isoellipticines 10-12 tethered through the indole nitrogen was synthesized and screened for antitumor cytotoxicity in the L-1210 murine leukemia assay. Activity was only displayed by 1,10-bis(6-ellipticinyl)-?-decane (8).
A convenient access to 1,3-disubstituted furo[3,4-b]indoles by acid ion-exchange resin-catalyzed furan formation
Basset, Joan,Romero, Manel,Serra, Tha?s,Pujol, M. Dolors
scheme or table, p. 356 - 362 (2012/01/06)
Efficient synthesis of furo[3,4-b]indoles starting from the corresponding indole is reported. The first route involves derivatization, protection, and deprotection steps, which stretch the syntheses. The second method provides a shorter and more efficient strategy to accessing the furoindole. The innovation starts with alkylation at C-2 of the indole presenting at the C-3 position a ketone-acetal, followed by the cycloaromatization catalyzed by polymeric ion-exchange resins. The second route represents a significant improvement over other methods previously described.
A NEW PRECURSOR TO 3,4-DIDEHYDROPYRIDINE, AND ITS USE IN THE SYNTHESIS OF THE ANTITUMOR ALKALOID ELLIPTICINE
May, Christopher,Moody, Christopher J.
, p. 247 - 250 (2007/10/02)
A concise synthesis of the antitumor alkaloid ellipticine (1) is reported.The route involves a Diels-Alder reaction between 1,4-dimethylpyranoindol-3-one (3), easily prepared in two steps from indole, and 3,4-didehydropyridine (4), and for its successful execution required the development of a new thermal, reagent-free precursor to the aryne.This precursor, 3-(3,3-dimethyltriazen-1-yl)pyridine-4-carboxylic acid (10a), prepared from 3-aminopyridine-4-carboxylic acid, decomposes in boiling acetonitrile to generate 3,4-didehydropyridine which can be intercepted in Diels-Alder reactions with tetraphenylcyclopentadienone, furan, and 2,5-dimethylfuran.The triazenes (10b) and (10c) can be prepared and decomposed similarly.The key Diels-Alder reaction between the pyranoindolone (3) and 3,4-didehydropyridine (4) gives ellipticine (1) in 20 percent yield, together with an equal amount of isoellipticine (14).
Synthesis and Diels-Alder Reactions of 1,3-Dimethyl-4-(phenylsulfonyl)-4H-furoindole. A new Annulation Strategy for the Construction of Ellipticine and Isoellipticine
Gribble, Gordon W.,Saulnier, Mark G.,Sibi, Mukund P.,Obaza-Nutaitis, Judy A.
, p. 4518 - 4523 (2007/10/02)
The novel fused heterocycle 1,3-dimethyl-4-(phenylsulfonyl)-4H-furoindole (4) is synthesized from 3-ethylindole (6) in six steps (46percent yield) or from indole-3-carboxaldehyde (12) in four steps (21percent yield).Furoindole 4 undergoes Diels-Alder reactions with dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne, and 3,4-pyridyne (5) to give the expected adducts 17, 18a,b, 19, and 23a,b, respectively.Deoxygenation and desulfonylation of 19 and 23a,b, respectively, give benzocarbazole 22 and a readily separable mixture of the pyridocarbazole alkaloids ellipticine (1a) and isoellipticine (2a).
