[OH:1][C@H:2]1[C@@H:14]2[C@@H:10]([C@@H:11]([O:16][CH3:17])[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]2.C(=O)([O-])O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:17][O:16][C@@H:11]1[C@H:10]2[CH2:9][C@@H:8]3[C@@H:3]([C:2](=[O:1])[C@H:14]2[C@H:13]([CH3:15])[O:12]1)[CH2:4][CH2:5][CH2:6][CH2:7]3To 1.23 g(5.12 mmol) of (1S,3S,3aS,4R,4aS,8aR,9aS)-4-hydroxy-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan and 3.26 g of sodium hydrogencarbonate in 100 ml of methylene chloride suspension were added 3.26 g(1.5 equivalents) of Dess-Martin reagent under stirring and cooling with ice, and the mixture was stirred for 1 hour at room temperature. After 6.35 g of sodium thiosulfate 5-hydrate and 50 ml of saturated aqueous solution of sodium hydrogencarbonate were added to the reaction mixture and stirred, two layers were separated and extraction with methylene chloride(5 ml×3) was performed from aqueous layer. The organic layers were dried over anhydrous magnesium sulfate, filtered and solvent was distilled off. The residue was purified by means of silica gel column chromatography(hexane:ethyl acetate=4:1) to obtain 1.18 g of (1S,3S,3aR,4aS,8aR,9aS)-1-methoxy-3-methyl-4-oxo-dodecahydronaphtho[2,3-c]furan (yield 97%).
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