Stereoselective total syntheses of (-)-desoxoprosopinine and (-)-desoxoprosophylline: Palladium(0)-catalyzed intramolecular N-alkylation for the key piperidine ring formation

Article abstract of DOI:10.1016/S0040-4020(01)85638-6

Intramolecular N-alkylation of D-glucose-derived substrate 21E proceeded in an S(N)2' mode smoothly in the presence of a Pd(0) catalyst and n-Bu₄NI. The major cyclization product, a 2,6-dialkylated piperidine 22t, was effectively converted into the title alkaloids.