title: Brief, efficient and highly diastereoselective synthesis of (±)-pumiliotoxin C based on the generation of an octahydroquinoline precursor via a four-component reaction.
abstract: A short and highly diastereoselective synthesis of the amphibian alkaloid pumiliotoxin C is described, based on the preparation of an octahydroquinoline derivative through a four-component reaction. The route proceeds in 66% overall yield from 1,3-cyclohexanedione and includes two hydrogenation steps, whose stereochemical outcome was controlled via nitrogen acylation.
authors.affiliation: Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid, Spain.
authors.forename: Swarupananda
authors.initials: S
authors.lastname: Maiti
authors.forename: J Carlos
authors.initials: JC
authors.lastname: Menéndez
mesh_terms: D000215:Acylation; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D009584:Nitrogen / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D011804:Quinolines; C011093:pumiliotoxin C; C037219:quinoline; D009584:Nitrogen