Sodium Cyanide → Mangostin

Participants

Reaction Conditions

Reaction Steps

Conversion of 6,7-di-O-methyl-γ-mangostin to γ-mangostin: To a solution of 6,7-di-O-methyl-γ-mangostin (0.5 g) in DMSO (LR, 20 mL) was added sodium cyanide (1.0 g) at RT and the mixture was stirred at 190-200° C. for 6 h. The reaction mixture was cooled to ambient temperature and poured into ice cold water. The mixture was extracted with a mixture of ethyl acetate and THF (1:1, 5×100 mL). The combined organic layer was washed with aqueous potassium permanganate (10%), water, brine and dried over sodium sulfate. The solution was filtered and the solvent evaporated. The residue was chromatographed over silica gel column using chloroform/methanol mixture (95:5) as eluent to give α-mangostin (330 mg, 68%). The α-mangostin was then converted to γ-mangostin using the inventive demethylation procedure as described in example 12.

Provenance & Evidence