1.1: 100 percent / diethyl ether; tetrahydrofuran / 0.67 h / 20 °C 2.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C 3.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 4.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 5.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 5.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 6.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 7.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 8.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 9.1: pyridine / CHCl3 / 3 h / 20 °C 10.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C View Scheme

1.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C 2.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 3.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 4.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 4.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 5.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 6.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 7.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 8.1: pyridine / CHCl3 / 3 h / 20 °C 9.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C View Scheme

1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 2: pyridine / CHCl3 / 3 h / 20 °C 3: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C View Scheme

1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 2: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 3: pyridine / CHCl3 / 3 h / 20 °C 4: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C View Scheme

1: pyridine / CH2Cl2 / 0.5 h / 0 °C 2: n-BuLi / hexane; tetrahydrofuran / 18 h / Ambient temperature 3: 92 percent / K2Os2(OH)4, (DHQD)2PHAL, K2CO3, potassium ferricyanate, CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 96 h / Ambient temperature 4: 1) CH3SO2Cl, pyridine, 2) K2CO3 / 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h View Scheme

1: n-BuLi / hexane; tetrahydrofuran / 18 h / Ambient temperature 2: 92 percent / K2Os2(OH)4, (DHQD)2PHAL, K2CO3, potassium ferricyanate, CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 96 h / Ambient temperature 3: 1) CH3SO2Cl, pyridine, 2) K2CO3 / 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h View Scheme

1: 95 percent / pyridine 2: 71 percent / Heating 3: 1) O3, 2) NaBH4 / CH2Cl2 4: 88 percent / Py 5: 87 percent / KI / acetone 6: 92 percent / dimethylformamide / 3 h / Heating 7: 81 percent / butyllithium / tetrahydrofuran; pentane / Ambient temperature 8: 74 percent / Li, NH3, ethanol / tetrahydrofuran / 0.5 h / -78 °C 9: 87 percent / glacial AcOH / 6 h / Ambient temperature 10: 92 percent / K2Os2(OH)4, (DHQD)2PHAL, K2CO3, potassium ferricyanate, CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 96 h / Ambient temperature 11: 1) CH3SO2Cl, pyridine, 2) K2CO3 / 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h View Scheme

1: 88 percent / Py 2: 87 percent / KI / acetone 3: 92 percent / dimethylformamide / 3 h / Heating 4: 81 percent / butyllithium / tetrahydrofuran; pentane / Ambient temperature 5: 74 percent / Li, NH3, ethanol / tetrahydrofuran / 0.5 h / -78 °C 6: 87 percent / glacial AcOH / 6 h / Ambient temperature 7: 92 percent / K2Os2(OH)4, (DHQD)2PHAL, K2CO3, potassium ferricyanate, CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 96 h / Ambient temperature 8: 1) CH3SO2Cl, pyridine, 2) K2CO3 / 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h View Scheme

1: 92 percent / dimethylformamide / 3 h / Heating 2: 81 percent / butyllithium / tetrahydrofuran; pentane / Ambient temperature 3: 74 percent / Li, NH3, ethanol / tetrahydrofuran / 0.5 h / -78 °C 4: 87 percent / glacial AcOH / 6 h / Ambient temperature 5: 92 percent / K2Os2(OH)4, (DHQD)2PHAL, K2CO3, potassium ferricyanate, CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 96 h / Ambient temperature 6: 1) CH3SO2Cl, pyridine, 2) K2CO3 / 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h View Scheme

1: 81 percent / butyllithium / tetrahydrofuran; pentane / Ambient temperature 2: 74 percent / Li, NH3, ethanol / tetrahydrofuran / 0.5 h / -78 °C 3: 87 percent / glacial AcOH / 6 h / Ambient temperature 4: 92 percent / K2Os2(OH)4, (DHQD)2PHAL, K2CO3, potassium ferricyanate, CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 96 h / Ambient temperature 5: 1) CH3SO2Cl, pyridine, 2) K2CO3 / 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h View Scheme