Total syntheses of (+/-)-beta-erythroidine and (+/-)-8-oxo-beta-erythroidine by an intramolecular Diels-Alder cycloaddition of a 2-amidoacrolein.
[reaction: see text] The total syntheses of (+/-)-beta-erythroidine and (+/-)-8-oxo-beta-erythroidine are described. The tetracyclic ring system of the natural products was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of an amidodioxin, an intramolecular Heck reaction, and a 6pi-electrocyclic ring closure of a dienoic acid.
He
Yong
Y
Department of Chemistry, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
Funk
Raymond L
RL
D000171:Acrolein / Q000031:analogs & derivatives* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004079:Dihydro-beta-Erythroidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
C520053:2-amidoacrolein; C520051:8-oxo-beta-erythroidine; D004079:Dihydro-beta-Erythroidine; C004873:beta-erythroidine; D000171:Acrolein