Sodium Cyanide → Mangostin

Participants

Reaction Conditions

Reaction Steps

γ-Mangostin from 3,6,7-trimethyl-γ-mangostin: To a solution of 3,6,7-trimethyl-γ-mangostin (0.5 g, 1.14 mmol) in DMSO (LR, 20 mL) was added sodium cyanide (1.0 g, 20.5 mmol) at RT and the mixture was stirred at 190-200° C. for 6 h. The reaction mixture was allowed to ambient temperature and poured into ice cold water and 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 under vacuum and the residue was chromatographed over silica gel column using chloroform-methanol mixture (95:5) as eluents to give α-mangostin (300 mg, 64%). The α-mangostin was then converted to γ-mangostin using the inventive demethylation procedure as described in example 12.

Provenance & Evidence