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

par Plehiers, Mark ;Hootele, Claude
Référence Canadian journal of chemistry, 74, 12, page (2444-2453)
Publication Publié, 1996-12

Article révisé par les pairs

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Résumé :

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.