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: 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 8: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 9: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 10: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 11: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 12: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 13: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °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 8: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 9: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 10: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 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 8: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 9: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 10: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 11: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 12: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 13: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 14: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 15: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °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 8: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 9: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 10: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 11: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 12: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 13: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 14: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 15: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C 16: pyridine / 2 h / 20 - 25 °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 8: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 9: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 10: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 11: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 12: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 13: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 14: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C 15: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °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 8: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 9: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 10: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 11: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 12: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 13: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 14: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °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 View Scheme