A tandem cascade cyclization-electrophilic aromatic substitution: application in the total synthesis of (+)-angelichalcone.
When cascade cyclizations initiated by Lewis acid-mediated opening of an epoxide are terminated through reaction with a MOM-protected phenol, a tandem electrophilic aromatic substitution can be obtained. This highly regioselective tandem process has been employed in the first synthesis of (+)-angelichalcone.
Topczewski
Joseph J
JJ
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA.
Callahan
Michael P
MP
Neighbors
Jeffrey D
JD
Wiemer
David F
DF
D002599:Chalcone / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D013237:Stereoisomerism; D013379:Substrate Specificity; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry*
D014966:Xanthenes; C546160:angelichalcone; D002599:Chalcone