Synthesis of β-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration

Abstract

The β-hydroxypiperidine alkaloids (±)-pseudoconhydrine, (±)-N-methylpseudoconhydrine, (−)-5-hydroxysedamine, and (+)-sedacryptine were synthesized. Successive functionalization of the piperidine ring via anodic methoxylation allowed the regio- and stereoselective introduction of the substituents. The α and α′ substituents were introduced by application of the sequence elimination–nucleophilic addition from 2- or 2,5-substituted 6-methoxycarbamates. Hydroboration – oxidation of enecarbamates, obtained by elimination of methanol from α-methoxycarbamates, allowed the introduction of the β-hydroxy function. Key words: alkaloid, Sedum, N-acyliminium, enecarbamate.