1: 1.) LiAlH4, 2.) NaIO4, 3.) NaBH4 2: DMAP / pyridine View Scheme

1: 1.) LiAlH4, 2.) NaIO4, 3.) NaBH4 2: DMAP / pyridine 3: 85 percent / Pd(PPh3)4 / dimethylformamide / 55 °C 4: OsO4, trimethylamine oxide 5: NH3 View Scheme

1: 1.) LiAlH4, 2.) NaIO4, 3.) NaBH4 2: DMAP / pyridine 3: 43 percent / Pd(PPh3)4 / dimethylformamide / 55 °C 4: NaOH / tetrahydrofuran; H2O 5: OsO4, trimethylamine N-oxide 6: NH3 View Scheme