Synthesis of the tricyclic core of alkaloid securinol B using a cascade of Vilsmeier-Haack and Mannich cyclizations.
Iminium ions generated upon amide activation were trapped sequentially with tethered nucleophiles. This cascade of cyclizations constitutes a new synthetic strategy that was applied to the construction of the tricyclic core of alkaloid securinol B.
Larouche-Gauthier
Robin
R
Département de Chimie, Université de Sherbrooke, 2500 boulevard Université, Sherbrooke, Québec J1K 2R1, Canada.
Bélanger
Guillaume
G
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008352:Mannich Bases / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D008352:Mannich Bases; C533294:securinol B