195311-92-3Relevant academic research and scientific papers
A simple and efficient synthetic route to chiral isopavines. Synthesis of (-)-O-methylthalisopavine and (-)-amurensinine
Carrillo, Luisa,Badia, Dolores,Dominguez, Esther,Vicario, Jose L.,Tellitu, Imanol
, p. 6716 - 6721 (1997)
The isopavinan alkaloids (-)-O-methylthalisopavine (7a) and (-)- amurensinine (7d) have been synthesized in good yield and high ee from the appropriate 1,2-diarylethylamine derivatives using optically active β-amino alcohols as chiral support. This synthetic route employs as key steps the alkylation reaction of the azomethine derivatives 2 with Grignard reagents 1 and-a novel one-pot double-intramolecular cyclization of the adequately functionalized 1,2-diarylethylamines 5 to afford a series of optically active isopavines 6a-d and 7a-d.
