Sodium Cyanide → Mangostin

HRID 1257136Notes

Reaction equation

HRID 1257136 reaction equation
[CH3:1][C:2]([CH3:29])=[CH:3][CH2:4][C:5]1[C:6]([OH:28])=[CH:7][C:8]2[O:27][C:15]3[CH:16]=[C:17]([OH:26])[C:18]([OH:25])=[C:19]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[C:14]=3[C:12](=[O:13])[C:9]=2[C:10]=1[OH:11].[C-:30]#N.[Na+]>CS(C)=O>[CH3:1][C:2]([CH3:29])=[CH:3][CH2:4][C:5]1[C:10]([OH:11])=[C:9]2[C:12]([C:14]3[C:15]([O:27][C:8]2=[CH:7][C:6]=1[OH:28])=[CH:16][C:17]([OH:26])=[C:18]([O:25][CH3:30])[C:19]=3[CH2:20][CH:21]=[C:22]([CH3:23])[CH3:24])=[O:13]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 5464078gamma-Mangostin

Product 1

HCID 5281650MangostinYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
195 °C

Procedure

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.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. additionpoured into ice cold water
  3. extractionThe mixture was extracted with a mixture of ethyl acetate and THF (1:1, 5×100 mL)
  4. washThe combined organic layer was washed with aqueous potassium permanganate (10%), water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent evaporated
  8. customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-582baa7ded5f49f9b158dda311bc71ae
Source dataset
uspto-grants-2013_06
Patent number
US08461360B2

Reaction notes

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