title: Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton.
abstract: The first enantioselective synthesis of trans-(6aS,11aR)-pterocarpan [(+)-2] and its conversion to cis-(6aS,11aS)-pterocarpan [(+)-1] was achieved starting from racemic 2'-benzyloxyflavanone (rac-3). Their stereochemistry was deduced by X-ray analysis of the ketal intermediate (-)-5a. The CD study of (+)-1 and (+)-2 allows the configurational assignment of similar pterocarpan derivatives by CD spectroscopy.
authors.affiliation: Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary.
authors.forename: Loránd
authors.initials: L
authors.lastname: Kiss
authors.forename: Tibor
authors.initials: T
authors.lastname: Kurtán
authors.forename: Sándor
authors.initials: S
authors.lastname: Antus
authors.forename: Attila
authors.initials: A
authors.lastname: Bényei
mesh_terms: D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D036343:Pterocarpans / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D036343:Pterocarpans