1: 83.4 percent / diisobutyl aluminum hydride / diethyl ether; hexane / -20 °C 2: 1.) Ti(i-PrO)4, (+)-diethyl tartrate, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 2.) CH2Cl2, -20 deg C, overnight 3: 88 percent / pyridine / 16 h / 5 °C 4: H2 / 10percent Pd/C / methanol / 6 h / 2585.7 Torr 5: 10percent aq. KOH / methanol / 0.5 h / Ambient temperature 6: 2 h / Heating 7: 1.) NaIO4, 2.) NaBH4 / 1.) ethanol, water, 10 min, 2.) ethanol, water, 10 min View Scheme

1: 83.4 percent / diisobutyl aluminum hydride / diethyl ether; hexane / -20 °C 2: 1.) Ti(i-PrO)4, (+)-diethyl tartrate, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 2.) CH2Cl2, -20 deg C, overnight 3: 88 percent / pyridine / 16 h / 5 °C 4: H2 / 10percent Pd/C / methanol / 6 h / 2585.7 Torr 5: 10percent aq. KOH / methanol / 0.5 h / Ambient temperature 6: 2 h / Heating 7: 1.) NaIO4, 2.) NaBH4 / 1.) ethanol, water, 10 min, 2.) ethanol, water, 10 min View Scheme