1: aq. NaOH 2: Br2 / Irradiation 3: aq. NaOH View Scheme

1: 30 percent / NaAlH2Et2 / toluene; diethyl ether / 16 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / acetic acid / 16 h / 30 °C / 22501.8 Torr 3: 1) lithiumdiisopropylamide / 1) THF/hexane, -78 deg C, 2) -25 deg C, 30 min 4: 1) CH2O, diethylamine, 2) NaOAc / 1) H2O, reflux, 30 min, 2) glacial acetic acid, reflux, 15 min View Scheme

1: 30 percent / NaAlH2Et2 / toluene; diethyl ether / 16 h / Ambient temperature 2: 99 percent / H2 / 10percent Pd/C / acetic acid / 16 h / 30 °C / 22501.8 Torr View Scheme