Chiroptical properties and synthesis of enantiopure cis and trans pterocarpan skeleton.
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.
Kiss
Loránd
L
Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary.
Kurtán
Tibor
T
Antus
Sándor
S
Bényei
Attila
A
D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D036343:Pterocarpans / Q000737:chemistry*; D013237:Stereoisomerism
D036343:Pterocarpans