title: Total synthesis of (+/-)-lennoxamine and (+/-)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins.
abstract: Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins constitute the key steps in the total syntheses of lennoxamine and aphanorphine. The aldehyde moiety of one cyclization product was transformed to a double bond, which was then engaged in a radical cyclization to produce the complete ring system of lennoxamine. The aldehyde functionality of the other cyclization product was converted to the corresponding mesylate, which underwent intramolecular displacement by a lactam enolate to furnish the ring system of aphanorphine. [reaction: see text]
authors.affiliation: Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
authors.forename: J R
authors.initials: JR
authors.lastname: Fuchs
authors.forename: R L
authors.initials: RL
authors.lastname: Funk
mesh_terms: D000171:Acrolein / Q000138:chemical synthesis*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D004146:Dioxanes / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*
chemical_list: D001952:Bridged-Ring Compounds; D004146:Dioxanes; D006571:Heterocyclic Compounds; D011758:Pyrroles; C434304:aphanorphine; C442893:lennoxamine; D000171:Acrolein