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

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