[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:10][CH2:11][CH2:12][CH:13]1[CH2:19][CH2:18][C:17]2[C:20]([O:30][CH3:31])=[C:21]([O:28][CH3:29])[C:22]([O:26][CH3:27])=[C:23]([O:24][CH3:25])[C:16]=2[CH2:15][CH2:14]1)(=O)C.Cl>C(OCC)C.O>[CH3:25][O:24][C:23]1[C:16]2[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][OH:10])[CH2:19][CH2:18][C:17]=2[C:20]([O:30][CH3:31])=[C:21]([O:28][CH3:29])[C:22]=1[O:26][CH3:27]
To a suspension of lithium aluminum hydride (486 mg) in diethyl ether (20 ml) was dropwise added a solution of 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate (3.00 g) in diethyl ether (10 ml) with cooling with ice. After the reaction mixture stirred for 30 min, 10% hydrochloric acid was added to the reaction mixture, which was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate, water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=1:1) to yield the entitled compound (2.60 g) as crystals.
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