Sodium Cyanide → Mangostin

HRID 1257134Notes

Reaction equation

HRID 1257134 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 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
195 °C

Procedure

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.

Workup

  1. customwas allowed to ambient temperature
  2. additionpoured into ice cold water
  3. extractionextracted 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 under vacuum
  8. customthe residue was chromatographed over silica gel column

Sources & evidence

ORD record
ord-9de0dbe6ab12431880be2aa3d17e7ce8
Source dataset
uspto-grants-2013_06
Patent number
US08461360B2

Reaction notes

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