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