1: Ti(O-i-Pr)2(N3)2 / benzene / Heating 2: H2 / Pd/C / ethyl acetate / 20 °C View Scheme

1: Ti(O-i-Pr)2(N3)2 / benzene / Heating 2: H2 / Pd/C / ethyl acetate / 20 °C 3: Ph3P; diisopropyl azodicarboxylate / CHCl3 / Heating View Scheme

1: Ti(O-i-Pr)2(N3)2 / benzene / Heating 2: H2 / Pd/C / ethyl acetate / 20 °C 3: Ph3P; diisopropyl azodicarboxylate / CHCl3 / Heating View Scheme

1: periodic acid; RuCl3 2: NaN3 / Cu(NO3)2 / H2O / 1.5 h / 65 °C 3: NaBH4 / Cu(NO3)2 / H2O / 0.5 h / 0 °C View Scheme

1: 2.7 g / titanium tetraisopropoxide, azidotrimethylsilane / benzene / 0.25 h / Heating 2: 1.) 2-acetoxyisobutyryl chloride, 2.) NaOMe / 1.) chloroform, RT, 5 h, 2.) THF, RT, 3 h 3: 9.63 g / propan-2-ol / 80 °C 4: 4.68 g / H2 / 10percent Pd/C / tetrahydrofuran; methanol; acetic acid / 12 h View Scheme

1: Ti(iPrO)2(N3)2 / benzene / 75 °C 2: 66 percent / H2 / 10 percent Pd/C / methanol / 760 Torr 3: 74 percent / NaHCO3 / H2O / 50 °C 4: 69 percent / PPh3; DEAD / CHCl3 / Heating View Scheme

sodium periodate 1.) Cl(CH2)2Cl-toluene, 83 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 0.25 h / 70 °C / Inert atmosphere 2.1: 4-(N,N-dimethlyamino)pyridine; di(n-butyl)tin oxide; triethylamine / dichloromethane / 3 h / 0 - 20 °C 3.1: potassium carbonate / methanol / 1 h / 0 - 25 °C 4.1: (S,S)-(salen)Co(OAc) complex; water / tetrahydrofuran / 14 h / 0 - 25 °C 5.1: isopropyl alcohol / 5 h / 50 °C 6.1: triethylamine / dichloromethane / 12.5 h / 0 - 20 °C 7.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 25 °C 7.2: 29 h 8.1: triethylamine / dichloromethane / 2 h / 25 °C View Scheme