in tetrahydrofuran; diethyl ether T=-78°C; 0.5 h;

1: 99 percent / NaBH4 / methanol / 0.5 h / 20 °C 2: 72 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C 3: 32 percent / aq. NaIO4 / methanol / 0.75 h / 20 °C 4: 72 percent / 240 h / 20 °C 5: 80 percent / KOH / methanol / 30 °C 6: Et3N; SOCl2 / tetrahydrofuran / 7 h / -78 °C 7: aq. NMO; OsO4 / acetone / 3 h / 20 °C 8: 151 mg / aq. NaIO4 / acetone / 2 h / 20 °C 9: 89 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C View Scheme

1: 72 percent / 240 h / 20 °C 2: 80 percent / KOH / methanol / 30 °C 3: Et3N; SOCl2 / tetrahydrofuran / 7 h / -78 °C 4: aq. NMO; OsO4 / acetone / 3 h / 20 °C 5: 151 mg / aq. NaIO4 / acetone / 2 h / 20 °C 6: 89 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C View Scheme

1: 72 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C 2: 32 percent / aq. NaIO4 / methanol / 0.75 h / 20 °C 3: 72 percent / 240 h / 20 °C 4: 80 percent / KOH / methanol / 30 °C 5: Et3N; SOCl2 / tetrahydrofuran / 7 h / -78 °C 6: aq. NMO; OsO4 / acetone / 3 h / 20 °C 7: 151 mg / aq. NaIO4 / acetone / 2 h / 20 °C 8: 89 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C View Scheme

1: 32 percent / aq. NaIO4 / methanol / 0.75 h / 20 °C 2: 72 percent / 240 h / 20 °C 3: 80 percent / KOH / methanol / 30 °C 4: Et3N; SOCl2 / tetrahydrofuran / 7 h / -78 °C 5: aq. NMO; OsO4 / acetone / 3 h / 20 °C 6: 151 mg / aq. NaIO4 / acetone / 2 h / 20 °C 7: 89 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C View Scheme

1: Et3N; SOCl2 / tetrahydrofuran / 7 h / -78 °C 2: aq. NMO; OsO4 / acetone / 3 h / 20 °C 3: 151 mg / aq. NaIO4 / acetone / 2 h / 20 °C 4: 89 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C View Scheme

1: 80 percent / KOH / methanol / 30 °C 2: Et3N; SOCl2 / tetrahydrofuran / 7 h / -78 °C 3: aq. NMO; OsO4 / acetone / 3 h / 20 °C 4: 151 mg / aq. NaIO4 / acetone / 2 h / 20 °C 5: 89 percent / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C View Scheme