106367-89-9Relevant academic research and scientific papers
A Simple Total Synthesis of the Isoindolobenzazepine Alkaloids Lennoxamine and Chilenamine
Napolitano, Elio,Spinelli, Guido,Fiaschi, Rita,Marsili, Antonio
, p. 785 - 788 (2007/10/02)
Lennoxamine (8) and chilenamine (9) have been synthesized from 3-(3,4-methylenedioxybenzylidene)-6,7-dimethoxyphthalide (1) in four and five high-yielding steps, respectively.The key step of the process is the cyclization, by intramolecular alkylation, of 3-(3,4-methylenedioxybenzyl)-6,7-dimethoxyphthalimidin-2-ylacetaldehyde dimethyl acetal (3) to 13,13a-dihydro-3,4-dimethoxy-10,11-methylenedioxyisoindolobenzazepin-5-one (7).Attempts to prepare (3) by base-catalysed cyclization of 3,4-dimethoxy-3',4'-methylenedioxystilbene-2-(2,2-dimethoxyethyl)carboxamide (15) were unsuccesful.
