C1CCCCC1.[C:7]([O:11][C:12]([N:14]1[C:22]2[C:17](=[C:18]([C:23]#[C:24][Si](C)(C)C)[CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH3:29])=[O:13])([CH3:10])([CH3:9])[CH3:8].[OH-:30].[Na+].[OH:32]O>O1CCCC1>[C:7]([O:11][C:12]([N:14]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:23][C:24]([OH:32])=[O:30])[C:17]=2[CH:16]=[C:15]1[CH3:29])=[O:13])([CH3:10])([CH3:9])[CH3:8]A solution of cyclohexane (16.1 ml) in tetrahydrofuran (160 ml) was cooled at −10° C., and then to the mixture was added dropwise borane-tetrahydrofuran complex (1M, 80 ml), and the mixture was stirred at 0° C. for 1 hour. To the solution was added dropwise a solution of 1-t-butoxycarbonyl-2-methyl-4-(2-trimethylsilylethynyl)indole (13.1 g; prepared in Reference Example 3) in tetrahydrofuran (60 ml), the mixture was stirred for 1 hour at room temperature. To a reaction solution was added dropwise 3N aqueous solution of sodium hydroxide (40 ml) and 30% hydrogen peroxide (in water, 45 ml), successively, and the mixture was stirred for 12 hours. The reaction mixture was extracted with water-diethyl ether. The aqueous layer was adjusted to acidic condition with hydrochloric acid and then extracted with ethyl acetate. The extraction was washed with water and a saturated aqueous solution of sodium chloride, successively, dried and concentrated under reduced pressure to give the title compound (10.4 g; crude).
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