1: 71 percent / t-BuOCl, L-(+)-diisopropyl tartrate, Ti(OiPr)4 / CH2Cl2 / -20 °C 2: 0.5N NaOH / 2-methyl-propan-2-ol / Heating 3: d-10-Camphersulfonic acid / CH2Cl2 / Ambient temperature 4: m-chloroperoxybenzoic acid / CH2Cl2 / -78 °C 5: NaOAc / Heating 6: LiAlH4 View Scheme

1: 73 percent / t-BuOCl, D-(-)-diisopropyl tartrate, Ti(OiPr)4 / CH2Cl2 / -20 °C 2: 0.5N NaOH / 2-methyl-propan-2-ol / Heating 3: d-10-Camphersulfonic acid / CH2Cl2 / Ambient temperature 4: m-chloroperoxybenzoic acid / CH2Cl2 / -78 °C 5: NaOAc / Heating 6: 41 percent / K2CO3 / methanol / Ambient temperature 7: NaBH4 View Scheme