1: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature 2: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight 3: 96 percent / CSA / 24 h / Ambient temperature 4: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature 5: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating View Scheme

1: 85 percent / Ti(O-iPr)4, (+)-L-diethyl tartrate, cumene hydroperoxide, 4 Angstroem MS / CH2Cl2 / 144 h / -25 °C 2: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h 3: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature View Scheme

1: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h 2: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature View Scheme

1: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C 2: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C 3: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h 4: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h 5: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C 6: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h 7: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C 8: pyridine, N,N-dimethylaminopyridine View Scheme

sodium hydroxide in methanol 3 h; Heating;

1: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating View Scheme

1: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h 2: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C 3: pyridine, N,N-dimethylaminopyridine View Scheme

1: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C 2: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h 3: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C 4: pyridine, N,N-dimethylaminopyridine View Scheme

1: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h 2: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h 3: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C 4: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h 5: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C 6: pyridine, N,N-dimethylaminopyridine View Scheme

1: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h 2: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C 3: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h 4: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C 5: pyridine, N,N-dimethylaminopyridine View Scheme