Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine.
Several novel cascade processes have been designed and developed that involve sequential reactions of imines and iminium ions to form substituted quinolizidine ring systems in a single step from simple and readily available starting materials. The utility and promise of these cascade reactions is evident from their application to extraordinarily concise syntheses of the representative quinolizidine alkaloids (+/-)-epilupinine and (-)-epimyrtine.
Amorde
Shawn M
SM
Department of Chemistry and Biochemistry, The University of Texas, Austin, 78712, USA.
Judd
Andrew S
AS
Martin
Stephen F
SF
D000470:Alkaloids / Q000032:analysis / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D011799:Quinazolines / Q000032:analysis / Q000138:chemical synthesis*; D013034:Sparteine / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D013237:Stereoisomerism; D000093843:Quinolizidine Alkaloids
D000470:Alkaloids; D007097:Imines; D011799:Quinazolines; D013034:Sparteine; C482086:epimyrtine; C015971:lupinine; D000093843:Quinolizidine Alkaloids