par Merlin, Patrick ;Braekman, Jean Claude ;Daloze, Désiré
Référence Tetrahedron, 47, 23, page (3805-3816)
Publication Publié, 1991
Article révisé par les pairs
Résumé : A stereocontrolled total synthesis of the ant alkaloid (±)-tetraponerine-8 (1) has been achieved in 7 steps and 28% overall yield, starting from 1-hydroxypiperidine. Key steps are a 1,3-dipolar cycloaddition (3 + 4 -> 5), a nucleophilic substitution (14 -> 15), and a reductive cyclization affording the tricyclic skeleton of tetraponerine-8 (15 -> 17).