1: POCl3; PCl5 / 180 °C 2: aqueous hydrochloric acid; tin 3: methanol. KOH-solution; palladium/barium carbonate / Hydrogenation View Scheme

1: trichlorophosphate / 6 h / 160 - 165 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / 6 h / Inert atmosphere; Reflux 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 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 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 View Scheme

T=170°C;

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 18: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C View Scheme

1: trichlorophosphate / 24 h / 130 °C 2: lithium hydroxide hydrate / tetrahydrofuran; water / 0.33 h / 25 °C 3: oxalyl dichloride / dichloromethane; tetrahydrofuran / 4 h / 25 °C 4: sodium azide / water; acetone / 0.03 h / 25 °C 5: trifluoroacetic acid / benzene / 21 h / 90 °C 6: potassium carbonate / methanol / 7.5 h / 25 °C 7: sulfuric acid; nitric acid / -5 °C 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 18: p-TSA*H2O / toluene; acetic acid / 18 h / 95 - 100 °C 19: pyridine / 2 h / 20 - 25 °C View Scheme

1.1: anhydrous tetramethylammonium chloride; trichlorophosphate / 16 h / 130 °C 1.3: pH 7 - 8 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; 1,4-dioxane / 18 h / 75 °C / Inert atmosphere 3.1: hydrogenchloride; water / 24 h / 65 °C View Scheme