• Citer

A revised structure for the piperidine alkaloid andrachamine

par Mill, Sibel ;Hootele, Claude
Référence Canadian journal of chemistry, 74, 12, page (2434-2443)
Publication Publié, 1996-12

Article révisé par les pairs

• Détails
• Contenu

Résumé :

A new method for the synthesis of trans-2,6-disubstituted piperidine derivatives is described. The transformation of cyclic α-methoxycarbamates 5 and 6 affords trans ketones 17 and 18. The synthesis of diols 1-4 from 17 and 18 has shown that the structure proposed in the literature for the piperidine alkaloid andrachamine is incorrect. A reexamination of the original spectral data of this alkaloid suggested that it is a meso 2,6-disubstituted piperidine derivative. Unambiguous syntheses of 23 and 24 and comparison with a sample of andrachamine have established that this alkaloid possesses structure 23.