in toluene; trifluoroacetic acid T=110°C; 2 h;

hydrogenchloride in tetrahydrofuran; water T=60°C; 3 h;

hydrogenchloride in tetrahydrofuran; water T=60°C; 3 h;

trifluoroacetic acid 3 h; Ambient temperature;

1: 98.1 percent / DMAP / CH2Cl2 / 4 h / 40 °C 2: aq. K2CO3 / methanol / Ambient temperature 3: 88.9 percent / 80percent aq. CF3COOH / 3 h / Ambient temperature View Scheme

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 11: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 12: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 13: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 14: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 15: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 16: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 17: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °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 10: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 11: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 12: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 13: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 14: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 15: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 16: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °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 9: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 10: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 11: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 12: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 13: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 14: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 15: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C View Scheme

1: 76 percent / PS-30 catalyst / various solvent(s) / 48 h 2: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 3: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 4: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 5: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 6: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 7: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C View Scheme

1: 100 percent / NaOCl, 4-acetoxy-TEMPO, KBr, NaHCO3 / CH2Cl2; H2O / 0.67 h 2: 96 percent / H2 / Pd/C / methanol / 96 h / 775.7 Torr / Ambient temperature; other catalyst, reaction time, temperature 3: 99 percent / TEMPO, KBr, NaHCO3, NaOCl / CH2Cl2; H2O / 0.5 h 4: 89 percent / TMSCl, NaI / acetonitrile / 6 h / 0 - 20 °C 5: 74 percent / Cs2CO3 / dimethylsulfoxide / 21 h / 47 - 50 °C 6: 93.4 percent / trifluoroacetic acid; toluene / 2 h / 110 °C View Scheme