Isoxanthohumol → Sophoraflavanone B

Participants

Reaction Steps

To a mixture of isoxanthohumol (50 mg, 0.14 mmol), KI (34 mg, 0.21 mmol) and Sc(OTf)3 (105 mg, 0.21 mmol), 10 ml of THF are added and the solution is heated for 2.5 h under reflux. The mixture is stirred overnight at room temperature and concentrated in vacuum. The scandium salt is separated off via a short silica gel column (eluted with CHCl3/methanol=100:1). The resultant solution is concentrated to dryness in vacuum, the residue is taken up in CHCl3 and eluted through a silica gel column using CHCl3/-methanol=100:1. 8-Prenylnaringenin (formula (III) where R1=prenyl, R2=H) (44 mg, 92%) is obtained as a light-yellowish solid.

Provenance & Evidence