A NEW AND FACILE STEREOSELECTIVE SYNTHESIS OF CIS-4a-ARYL-1,2,3,4,4a,5,6,8a-OCTAHYDROISOQUINOLINE DERIVATIVES

Article abstract of DOI:10.1246/cl.1982.1915

Cis-1,2,3,4,4a,5,6,8a-octahydro-2-methyl-4a-phenylisoquinolin-3-one was obtained by cyclization of the acyliminium ion intermediate, derived from the corresponding amide.Reduction of this cyclization product with LiAlH4 in THF afforded cis-1,2,3,4,4a,5,6,8a-octahydro-2-methyl-4a-phenylisoquinoline.In a similar way, the octahydro-4a-(2-methoxyphenyl)-isoquinolin-3-one was also prepared from the corresponding amide.