Smilagenone → Smilagenin

Participants

Reaction Steps

N-Selectride® (0.64 ml, 1M in THF) was added to a solution of smilagenone (206 mg) in THF (10 ml) over 10 minutes at −78° C. The mixture was stirred and quenched with 10% aqueous citric acid (2 g in 20 ml water) and the product extracted into DCM (2×50 ml), dried (MgSO4) and evaporated to a colourless oil. The oil was taken up in acetone (20 ml) and water (50 ml) added. The precipitate was collected by filtration and dried to afford smilagenin (200 mg, 97%).

Provenance & Evidence