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

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

1: 89 percent / DIBAH / CH2Cl2; toluene / 0.5 h / -78 °C 2: pyridine / CH2Cl2 / 0.5 h / 0 °C 3: n-BuLi / hexane; tetrahydrofuran / 18 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

1: 74 percent / Li, NH3, ethanol / tetrahydrofuran / 0.5 h / -78 °C 2: 87 percent / glacial AcOH / 6 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

pyridine; potassium carbonate; methanesulfonyl chloride 1) CH2Cl2, RT, 2) aq. CH3OH, RT, 18 h; Yield givenMultistep reaction;

1: pyridine / CH2Cl2 / 23 °C 2: K2CO3 / methanol 3: n-BuLi / tetrahydrofuran / -20 °C View Scheme

1: 85 percent / LiCl, DBU / CH2Cl2; acetonitrile 2: 93 percent / Mg(0) / methanol; benzene / 25 °C 3: 72 percent / DIBAL-H / toluene / -78 °C 4: 85 percent / KHMDS / tetrahydrofuran / -20 °C 5: Bu4NF / tetrahydrofuran / 23 °C 6: 82 percent / OsO4, (DHQD)2PYDZ / H2O; 2-methyl-propan-2-ol / 52 h / 0 °C 7: pyridine / CH2Cl2 / 23 °C 8: K2CO3 / methanol 9: n-BuLi / tetrahydrofuran / -20 °C View Scheme

1: Swern oxidn. / -40 °C 2: 85 percent / LiCl, DBU / CH2Cl2; acetonitrile 3: 93 percent / Mg(0) / methanol; benzene / 25 °C 4: 72 percent / DIBAL-H / toluene / -78 °C 5: 85 percent / KHMDS / tetrahydrofuran / -20 °C 6: Bu4NF / tetrahydrofuran / 23 °C 7: 82 percent / OsO4, (DHQD)2PYDZ / H2O; 2-methyl-propan-2-ol / 52 h / 0 °C 8: pyridine / CH2Cl2 / 23 °C 9: K2CO3 / methanol 10: n-BuLi / tetrahydrofuran / -20 °C View Scheme

1: DIBAL-H 2: Swern oxidn. / -40 °C 3: 85 percent / LiCl, DBU / CH2Cl2; acetonitrile 4: 93 percent / Mg(0) / methanol; benzene / 25 °C 5: 72 percent / DIBAL-H / toluene / -78 °C 6: 85 percent / KHMDS / tetrahydrofuran / -20 °C 7: Bu4NF / tetrahydrofuran / 23 °C 8: 82 percent / OsO4, (DHQD)2PYDZ / H2O; 2-methyl-propan-2-ol / 52 h / 0 °C 9: pyridine / CH2Cl2 / 23 °C 10: K2CO3 / methanol 11: n-BuLi / tetrahydrofuran / -20 °C View Scheme