1.1: methanol / 20 °C 1.2: magnesium sulfate / methanol / 20 °C 1.3: NaBH4 / methanol / 20 °C 2.1: sodium amide / toluene / Heating View Scheme

1.1: 74 percent / DMAP; Et3N / CH2Cl2 / 20 °C 2.1: LiHMDS / tetrahydrofuran / -78 °C 2.2: 80 percent / tetrahydrofuran / 20 °C 3.1: 74 percent / OsO4; NaIO4; H2O / tetrahydrofuran / 20 °C 4.1: methanol / 20 °C 4.2: magnesium sulfate / methanol / 20 °C 4.3: NaBH4 / methanol / 20 °C 5.1: sodium amide / toluene / Heating View Scheme

1.1: LiHMDS / tetrahydrofuran / -78 °C 1.2: 80 percent / tetrahydrofuran / 20 °C 2.1: 74 percent / OsO4; NaIO4; H2O / tetrahydrofuran / 20 °C 3.1: methanol / 20 °C 3.2: magnesium sulfate / methanol / 20 °C 3.3: NaBH4 / methanol / 20 °C 4.1: sodium amide / toluene / Heating View Scheme

1.1: 74 percent / OsO4; NaIO4; H2O / tetrahydrofuran / 20 °C 2.1: methanol / 20 °C 2.2: magnesium sulfate / methanol / 20 °C 2.3: NaBH4 / methanol / 20 °C 3.1: sodium amide / toluene / Heating View Scheme

1.1: 94 percent / SOCl2 / Heating 2.1: 74 percent / DMAP; Et3N / CH2Cl2 / 20 °C 3.1: LiHMDS / tetrahydrofuran / -78 °C 3.2: 80 percent / tetrahydrofuran / 20 °C 4.1: 74 percent / OsO4; NaIO4; H2O / tetrahydrofuran / 20 °C 5.1: methanol / 20 °C 5.2: magnesium sulfate / methanol / 20 °C 5.3: NaBH4 / methanol / 20 °C 6.1: sodium amide / toluene / Heating View Scheme

1: MgSO4 / methanol 2: NaBH4 / methanol / 20 °C 3: NaNH2 / toluene / Heating View Scheme

trifluoroacetic acid in dichloromethane T=20°C;