(+)-Methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate → (+)-Methyl 5-(3-formylphenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]([S:17][CH2:18][CH2:19][C:20](=[O:24])[N:21]([CH3:23])[CH3:22])[S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=1>C(OCC)(=O)C.[O-2].[Mn+2]>[CH:2]([C:3]1[CH:4]=[C:5]([CH:9]([S:17][CH2:18][CH2:19][C:20](=[O:24])[N:21]([CH3:23])[CH3:22])[S:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=1)=[O:1]Participants
4
Procedure
To a solution of (+)-methyl 5-(3-(hydroxymethyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (step 2) (679 mg) in ethyl acetate (30 mL) was added activated manganese oxide (1.3 g). The suspension was stirred overnight at room temperature. The suspension was filtered on a pad of silica gel and washed with EtOAc. The solvent was evaporated, affording the title compound.