Stereoselective Total Syntheses of (-)-Desoxoprosopinine and (-)-Desoxoprosophylline: Palladium(0)-Catalyzed Intramolecular N-Alkylation for the Key Piperidine Ring Formation

Abstract
Treatment of allylic chloride 18E, derived from D-glucose, with NaH in the presence of a catalytic amount of Pd(Ph3P)4 provided a piperidine derivative 19 with high diastereoselectivity. Further functional group transformation from 19 completed enantiospecific total syntheses of (-)-desoxoprosopinine 3 and (-)-desoxoprosophylline 4.

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