Sodium Acetate → Scillarenin

Participants

Reaction Steps

Proscillaridin (3 g, 5.6 mmol) was dissolved in ethanol (57 ml) at 40° C. while stirring, to this solution was added 171 ml of sodium acetate buffer (pH=4, 0.02 M) at 40° C., followed by naringinase (1.03 g). The reaction was stirred for 24 hours, when ethanol was added (200 ml) and the solvent was removed in vacuo, an additional 100 ml ethanol was added and the solvent was removed in vacuo. Material was purified by flash chromatography (DCM to 9:1 DCM:MeOH) to give 9 as an off-white solid (1.9 g, 4.9 mmol, 90%). 1H-NMR (CDCl3, 300 MHz): 7.89 (dd, J=9.7, 2.6 Hz, 1H), 7.26 (dd, J=2.6, 0.9 Hz, 1H), 6.27 (dd, J=9.7, 0.9, 1H), 5.31 (s, 1H), 4.31 (m, 1H), 2.47 (dd, J=9.3, 6.2 Hz, 1H), 2.25-0.98 (m, 19H), 1.04 (s, 3H), 0.73 (s, 3H) 13C-NMR (CDC13, 75 MHz): 163.28, 148.77, 147.59, 146.42, 123.90, 123.35, 115.22, 85.01, 67.65, 51.20, 50.38, 48.46, 42.65, 40.82, 37.58, 35.71, 32.65, 32.36, 29.17, 28.89, 28.76, 21.43, 19.10, 16.69.

Provenance & Evidence