HCID 11586634, compound → HCID 11528683, compound
Reaction equation
[CH3:1][C@H:2]([CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:3][C:4]#[C:5][CH:6]([OH:8])[CH3:7]>C1COCC1.[O-2].[O-2].[Mn+4]>[CH3:1][C@H:2]([CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:3][C:4]#[C:5][C:6](=[O:8])[CH3:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A 300 g (1.3255 mol) solution of (2RS,6S)-6-methyl-7-[(RS)-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxy]hept-3-in-2-ol, dissolved in 600 ml of THF, is added by stirring to a suspension of 1500 g manganese dioxide in 2250 ml of THF, and stirring is continued at room temperature for 48 hours. The suspension is then filtered over silica gel and the solvent is removed in vacuo. 280 g of the product is obtained.