71700-15-7Relevant articles and documents
Lead Tetraacetate Oxidation of Oxyprotoberberines. A Convenient Synthesis of 13-Oxygenated Berbines and Oxyprotoberberines.
Dorn, Clifford R.,Koszyk, Francis J.,Lenz, George R.
, p. 2642 - 2644 (1984)
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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
, 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.
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.
