71700-15-7Relevant academic research and scientific papers
Intramolecular chemoselective acylation of a suitably substituted isoindole: Synthesis of (±)-chilenine and (±)-deoxychilenine
Wakchaure, Prasad B.,Argade, Narshinha P.
, p. 2838 - 2842 (2011)
Starting from 3,4-dimethoxyhomophthalic anhydride and 6- bromohomopiperonylamine, concise and efficient syntheses of Chilean berberis products chilenine and deoxychilenine have been demonstrated via partially divergent routes by taking advantage of facile air-oxidation of homophthalimide along with intramolecular chemoselective acylation as the key steps. Georg Thieme Verlag Stuttgart - New York.
A new approach to isoindolobenzazepines via a ring-expansion of isoindoloisoquinoline: Synthesis of lennoxamine and chilenine
Koseki, Yuji,Kusano, Shuichi,Sakata, Harumi,Nagasaka, Tatsuo
, p. 2169 - 2172 (1999)
A convenient short-step synthesis of lennoxamine 1 and chilenine 2 is described. The key steps are the preparation of an acyliminium precursor and a novel expansion of the six-membered ring to a seven-membered ring.
A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps
Zhou, Shiqiang,Tong, Rongbiao
supporting information, p. 7084 - 7089 (2016/05/19)
A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.
A concise synthesis of chilenine via a sequential reaction process
Kim, Guncheol,Jung, Philguem,Tuan, Le Anh
, p. 2391 - 2392 (2008/09/18)
A new short synthesis of chilenine has been achieved in two steps. The precursor amide was readily prepared by the condensation of the corresponding amine and acid. Treatment of the amide with oxalyl chloride in the presence of AlCl3 at room te
Palladium-catalyzed intramolecular γ-lactam formation of an aryl halide and an enolate: Synthesis of isoindolobenzazepine alkaloids, lennoxamine, 13-deoxychilenine, and chilenine
Honda, Toshio,Sakamaki, Yoshiaki
, p. 6823 - 6825 (2007/10/03)
A facile synthetic path to isoindolobenzazepine alkaloids, lennoxamine, 13-deoxychilenine, and chilenine, was established by employing a palladium-catalyzed intramolecular α-arylation of the ketone, as the key step.
Lewis acid-promoted tandem desulfurization and hydroxylation of γ-phenylthio-substituted lactams: Novel synthetic strategy of isoindolobenzazepine alkaloid, chilenine
Yoda, Hidemi,Inoue, Kei-Ichi,Ujihara, Yasuaki,Mase, Nobuyuki,Takabe, Kunihiko
, p. 9057 - 9060 (2007/10/03)
Treatment of a variety of alicyclic and aromatic γ-phenylthio- substituted lactams with Lewis acids such as cuprous or cupric halides in aqueous solution at rt was found to undergo novel tandem desulfurization and hydroxylation reactions to generate γ-hydroxylated lactams without the ring-opened products in extremely high yields, respectively. This process was further applied to the total synthesis of an isoindolobenzazepine alkaloid, chilenine, by featuring the elaboration of the functionalized phthalimide derivative.
Total synthesis of lennoxamine and chilenine via ring-expansion of isoindoloisoquinoline to isoindolobenzazepine
Koseki, Yuji,Katsura, Shinya,Kusano, Shuichi,Sakata, Harumi,Sato, Hiroto,Monzene, Yoshinori,Nagasaka, Tatsuo
, p. 527 - 540 (2007/10/03)
Convenient synthesis of the benzazepine alkaloids, lennoxamine (1) and chilenine (2), is described. The key steps are conversion of methylenelactam (5) to an N-tertiary acyliminium ion precursor (16) and a novel expansion of the six-membered ring of 4 to a benzazepine ring system (3b), which could be transformed into lennoxamine (1) and chilenine (2).
THE TOTAL SYNTHESIS OF CHILENINE: NOVEL CONSTRUCTIONS OF CYCLIC ENAMIDES
Fang, Francis G.,Danishefsky, Samuel J.
, p. 2747 - 2750 (2007/10/02)
Tungsten hexacarbonyl or rhodium(II) acetate mediated reductive coupling of a dithiolane or 2,3-diphenyl-N-aziridinohydrazone respectively with a regioselectively activated unsymmetrical dimethoxyphthalimide provides the key step in a total synthesis of t
