1: With methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); (DHQD)2-PYR; potassium dioxotetrahydroxoosmate(VI) in water; tert-butyl alcohol T=0°C; Sharpless dihydroxylation; 40 h; 2: With iodine; calcium carbonate in methanol; water T=40°C; 15 h; Further stages.;

toluene-4-sulfonic acid in toluene 1 h; Heating;

1.1: chloro(trimethyl)silane; sodium iodide; H2O / acetonitrile / 5 h / 65 °C 2.1: 70 percent / potassium carbonate; lithium bromide; tetrabutylammonium bromide / H2O; toluene / Heating 3.1: 94 percent / lithium hydroxide monohydrate / H2O; tetrahydrofuran / cooling 4.1: oxalyl chloride / CH2Cl2; dimethylformamide / cooling 5.1: NaHCO3 / CH2Cl2 / 20 °C 6.1: 98 percent / triphenylphosphine oxide; trifluoromethanesulfonic anhydride / CH2Cl2 / 0 - 20 °C 7.1: K3Fe(CN)6; potassium carbonate; CH3SO2NH2 / (DHQD)2-PYR; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C 7.2: iodine; CaCO3 / methanol; H2O / 15 h / 40 °C View Scheme

1.1: 70 percent / potassium carbonate; lithium bromide; tetrabutylammonium bromide / H2O; toluene / Heating 2.1: 94 percent / lithium hydroxide monohydrate / H2O; tetrahydrofuran / cooling 3.1: oxalyl chloride / CH2Cl2; dimethylformamide / cooling 4.1: NaHCO3 / CH2Cl2 / 20 °C 5.1: 98 percent / triphenylphosphine oxide; trifluoromethanesulfonic anhydride / CH2Cl2 / 0 - 20 °C 6.1: K3Fe(CN)6; potassium carbonate; CH3SO2NH2 / (DHQD)2-PYR; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C 6.2: iodine; CaCO3 / methanol; H2O / 15 h / 40 °C View Scheme

1.1: 94 percent / lithium hydroxide monohydrate / H2O; tetrahydrofuran / cooling 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / cooling 3.1: NaHCO3 / CH2Cl2 / 20 °C 4.1: 98 percent / triphenylphosphine oxide; trifluoromethanesulfonic anhydride / CH2Cl2 / 0 - 20 °C 5.1: K3Fe(CN)6; potassium carbonate; CH3SO2NH2 / (DHQD)2-PYR; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C 5.2: iodine; CaCO3 / methanol; H2O / 15 h / 40 °C View Scheme

1.1: oxalyl chloride / CH2Cl2; dimethylformamide / cooling 2.1: NaHCO3 / CH2Cl2 / 20 °C 3.1: 98 percent / triphenylphosphine oxide; trifluoromethanesulfonic anhydride / CH2Cl2 / 0 - 20 °C 4.1: K3Fe(CN)6; potassium carbonate; CH3SO2NH2 / (DHQD)2-PYR; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C 4.2: iodine; CaCO3 / methanol; H2O / 15 h / 40 °C View Scheme

1.1: 98 percent / triphenylphosphine oxide; trifluoromethanesulfonic anhydride / CH2Cl2 / 0 - 20 °C 2.1: K3Fe(CN)6; potassium carbonate; CH3SO2NH2 / (DHQD)2-PYR; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C 2.2: iodine; CaCO3 / methanol; H2O / 15 h / 40 °C View Scheme

1.1: 97 percent / triethylamine / PdCl2(CH2Cl2)dppf / 5 h / 90 °C / 6205.94 Torr 2.1: chloro(trimethyl)silane; sodium iodide; H2O / acetonitrile / 5 h / 65 °C 3.1: 70 percent / potassium carbonate; lithium bromide; tetrabutylammonium bromide / H2O; toluene / Heating 4.1: 94 percent / lithium hydroxide monohydrate / H2O; tetrahydrofuran / cooling 5.1: oxalyl chloride / CH2Cl2; dimethylformamide / cooling 6.1: NaHCO3 / CH2Cl2 / 20 °C 7.1: 98 percent / triphenylphosphine oxide; trifluoromethanesulfonic anhydride / CH2Cl2 / 0 - 20 °C 8.1: K3Fe(CN)6; potassium carbonate; CH3SO2NH2 / (DHQD)2-PYR; K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C 8.2: iodine; CaCO3 / methanol; H2O / 15 h / 40 °C View Scheme

1: 20 h / 70 °C 2: 97 percent / acetic acid / 2 h / 70 °C 3: 96 percent / 2N aq. sulfuric acid / 1,2-dimethoxy-ethane / 8 h / 50 °C 4: 72 percent / p-toluenesulfonica acid / toluene / 1 h / Heating View Scheme

1: tBuLi 2: nBuLi, I2 3: 63 percent / Et3SiH / trifluoroacetic acid 4: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 5: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 6: 47 percent / ICl 7: 72 percent / aq. HI 8: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 9: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme