osmium(VIII) oxide; trimethylamine-N-oxide in tert-butyl alcohol T=40°C; 24 h;

1: 78 percent / POPCl3, Me4NCl / 2 h / 130 - 142 °C 2: 84 percent / tetrahydrofuran / 1 h / 0 °C 3: 100 percent / TMSCl / 12 h / Ambient temperature 4: 89 percent / methanol / 20 h / Heating 5: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 6: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 7: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 8: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 10: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 84 percent / tetrahydrofuran / 1 h / 0 °C 2: 100 percent / TMSCl / 12 h / Ambient temperature 3: 89 percent / methanol / 20 h / Heating 4: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 5: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 6: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 7: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 9: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 100 percent / TMSCl / 12 h / Ambient temperature 2: 89 percent / methanol / 20 h / Heating 3: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 4: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 5: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 6: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 8: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 89 percent / methanol / 20 h / Heating 2: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 3: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 4: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 5: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 7: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h 2: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 3: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 4: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 6: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 71 percent / NaBH4, n-Bu4NCl / H2O / 18 h 2: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 3: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 5: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C 2: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 4: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

1: 89 percent / Pd(OAc)2, K2CO3, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr 3: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme

2: 92 percent / OsO4, Me3NO*2H2O / 2-methyl-propan-2-ol / 24 h / 40 °C View Scheme