1: imidazole / dimethylformamide / 23 h / 0 °C 2: 1.90 g / NaOMe / methanol / 2 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: 97 percent / PPTS / CH2Cl2 / 1 h / 20 °C 2: 100 percent / NaOMe / methanol / 2 h / 20 °C 3: imidazole / dimethylformamide / 23 h / 0 °C 4: 3.82 g / aq. AcOH / tetrahydrofuran / 5 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: NaClO2; NH2SO3H; Na2HPO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 2: Et3N; DMAP; 1-hydroxybenzotriazol / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride / CH2Cl2 / 16 h / 20 °C View Scheme

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