4-(N,N-dimethlyamino)pyridine; benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane T=20°C; 16 h;

1: LiAlH4 / tetrahydrofuran / 20 h / 0 °C 2: 2.92 g / pyridine / 17 h / 20 °C 3: lipase PS (Amano); H2O / tetrahydrofuran / 480 h / 20 °C 4: imidazole / dimethylformamide / 23 h / 0 °C 5: 1.90 g / NaOMe / methanol / 2 h / 20 °C 6: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C 7: 85 percent / OsO4; H2O; Me3NO*2H2O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C 8: 89 percent / n-Bu3SnH; AIBN / toluene / 1 h / Heating 9: Pb(OAc)4 / benzene / 0.75 h / 20 °C 10: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 11: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 12: 96 percent / NaI / butan-2-one / 12 h / Heating 13: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 14: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 15: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 16: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 17: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 18: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 19: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 20: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: 2.92 g / pyridine / 17 h / 20 °C 2: lipase PS (Amano); H2O / tetrahydrofuran / 480 h / 20 °C 3: imidazole / dimethylformamide / 23 h / 0 °C 4: 1.90 g / NaOMe / methanol / 2 h / 20 °C 5: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C 6: 85 percent / OsO4; H2O; Me3NO*2H2O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C 7: 89 percent / n-Bu3SnH; AIBN / toluene / 1 h / Heating 8: Pb(OAc)4 / benzene / 0.75 h / 20 °C 9: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 10: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 11: 96 percent / NaI / butan-2-one / 12 h / Heating 12: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 13: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 14: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 15: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 16: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 17: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 18: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 19: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: lipase PS (Amano); H2O / tetrahydrofuran / 480 h / 20 °C 2: imidazole / dimethylformamide / 23 h / 0 °C 3: 1.90 g / NaOMe / methanol / 2 h / 20 °C 4: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C 5: 85 percent / OsO4; H2O; Me3NO*2H2O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C 6: 89 percent / n-Bu3SnH; AIBN / toluene / 1 h / Heating 7: Pb(OAc)4 / benzene / 0.75 h / 20 °C 8: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 9: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 10: 96 percent / NaI / butan-2-one / 12 h / Heating 11: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 12: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 13: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 14: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 15: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 16: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 17: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 18: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: imidazole / dimethylformamide / 23 h / 0 °C 2: 3.82 g / aq. AcOH / tetrahydrofuran / 5 h / 20 °C 3: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C 4: 85 percent / OsO4; H2O; Me3NO*2H2O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C 5: 89 percent / n-Bu3SnH; AIBN / toluene / 1 h / Heating 6: Pb(OAc)4 / benzene / 0.75 h / 20 °C 7: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 8: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 9: 96 percent / NaI / butan-2-one / 12 h / Heating 10: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 11: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 12: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 13: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 14: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 15: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 16: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 17: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: 100 percent / NaOMe / methanol / 2 h / 20 °C 2: imidazole / dimethylformamide / 23 h / 0 °C 3: 3.82 g / aq. AcOH / tetrahydrofuran / 5 h / 20 °C 4: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C 5: 85 percent / OsO4; H2O; Me3NO*2H2O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C 6: 89 percent / n-Bu3SnH; AIBN / toluene / 1 h / Heating 7: Pb(OAc)4 / benzene / 0.75 h / 20 °C 8: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 9: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 10: 96 percent / NaI / butan-2-one / 12 h / Heating 11: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 12: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 13: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 14: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 15: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 16: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 17: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 18: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 2: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 3: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 4: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 2: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 3: 96 percent / NaI / butan-2-one / 12 h / Heating 4: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 5: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 6: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 7: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 8: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 10: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 11: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C 2: 85 percent / OsO4; H2O; Me3NO*2H2O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C 3: 89 percent / n-Bu3SnH; AIBN / toluene / 1 h / Heating 4: Pb(OAc)4 / benzene / 0.75 h / 20 °C 5: 2.04 g / NaBH4 / methanol / 1 h / 20 °C 6: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 7: 96 percent / NaI / butan-2-one / 12 h / Heating 8: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C 9: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / benzene / 6 h / Heating 10: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 11: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 12: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 13: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 14: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 15: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

1: 96 percent / Br2 / diethyl ether / 1 h / -78 °C 2: 53 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 75 °C 3: 100 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C 4: Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 5: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 6: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme