HCID 11074968, compound → HCID 12011994, compound
Reaction equation
[OH:1][C@H:2]1[C@@H:14]2[C@@H:10]([C:11](=[O:16])[O:12][C@H:13]2[CH3:15])[CH:9]=[C:8]2[C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2>C(O)C.[Pt]=O>[OH:1][C@H:2]1[C@@H:14]2[C@@H:10]([C:11](=[O:16])[O:12][C@H:13]2[CH3:15])[CH2:9][C@@H:8]2[C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To 375.1 mg(1.69 mmol) of (3S,3aS,4R,4aS,9aS)-4-hydroxy-3-methyl-3a,4,4a,5,6,7,8,9a-octahydronaphtho[2,3-c]furan-1(3H)-one in 5 ml of ethanol solution were added 40.0 mg(10% by weight) of platinum oxide, and catalytic reduction was conducted at ambient temperature under 98.1 Kpa. After stirring for 16 hours, the reaction mixture was filtered through celite and the residue was washed using 20 ml of ethyl acetate. Combined organic layers were distilled off under reduced pressure and the residue was purified by means of silica gel column chromtography(methylene chloride:ethyl acetate=4:1) to obtain 363.7 mg of (3S,3aS,4R,4aS,8aR,9aS)-4-hydroxy-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one (yield 96%).