Hydrochloric Acid → Mangostin

Temperature

195 °C

γ-Mangostin from β-mangostin: To a solution of β-mangostin (0.25 g, 0.58 mmol) in DMSO (LR, 15 mL) was added sodium cyanide (0.52 g, 10.61 mmol) at RT and the mixture was stirred at 190-200° C. for 6 h. The reaction mixture was allowed to cool to ambient temperature and then poured into ice water and the mixture was acidified with dil. HCl. The solution was extracted with ethyl acetate (5×50 mL). The combined ethyl acetate layer was washed with aqueous potassium permanganate (10%), water, brine and dried over sodium sulfate. The solution was filtered and treated with few drops of triethyl amine and the solvent evaporated. The residue was chromatographed over silica gel column using hexane/ethyl acetate mixture (80:20) as an eluent to give α-mangostin (90 mg, 37%). The α-mangostin was then converted to γ-mangostin using the inventive demethylation procedure as described in example 12.

1. temperatureto cool to ambient temperature
2. extractionThe solution was extracted with ethyl acetate (5×50 mL)
3. washThe combined ethyl acetate layer was washed with aqueous potassium permanganate (10%), water, brine
4. dry with materialdried over sodium sulfate
5. filtrationThe solution was filtered
6. additiontreated with few drops of triethyl amine
7. customthe solvent evaporated
8. customThe residue was chromatographed over silica gel column

ORD record

ord-e29949fa0222415c96995968cd95f3fe

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461360B2