Total synthesis of (+/-)-lennoxamine and (+/-)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins.
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]
Fuchs
J R
JR
Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
Funk
R L
RL
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*
D001952:Bridged-Ring Compounds; D004146:Dioxanes; D006571:Heterocyclic Compounds; D011758:Pyrroles; C434304:aphanorphine; C442893:lennoxamine; D000171:Acrolein