1: 1 M LiBEt3H, 30percent H2O2 / tetrahydrofuran / 1.) -78 deg C, 30 min; 2.) 0 deg C, 20 min 2: p-TsOH*H2O / Ambient temperature 3: 1.) CuBr*Me2S, 2.) BF3*OEt2 / 1.) ether, -40 deg C, 45 min, 2.) -78 deg C, 30 min; 15 min; -78 deg C to room temp., 3 h; room temp., 1 h 4: TFA / CH2Cl2 / Ambient temperature View Scheme

Cp*RuCl{(C6H5)2P-(CH2)2NH2-κ2-P,N}; potassium tert-butylate; hydrogen in tert-butyl alcohol T=80°C; P=22502.3 Torr; 24 h; Autoclave;

1: With lithium triethylborohydride in tetrahydrofuran; toluene T=-70°C; 0.5 h; 2: With 4-(N,N-dimethlyamino)pyridine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride in tetrahydrofuran; toluene T=-70 - 20°C; 2 h;

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 2 h / -78 °C 2.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C 3.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C 5.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice 5.2: 16 h / 20 °C 6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7.1: tetraethyl ammonium fluoride / tetrahydrofuran / 16 h / Reflux 8.1: water; acetic acid / 1.5 h / Heating 9.1: pyridine / dichloromethane / 16 h / 20 °C 10.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C / Inert atmosphere 11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 11.2: 12 h / -78 - 0 °C 12.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 2 h / 2068.65 Torr 13.1: triethylamine / dichloromethane / 0.08 h / 20 °C 14.1: triethylamine / dichloromethane 15.1: trifluoroacetic acid / dichloromethane / 0.5 h View Scheme

1: 1.) lithium hexamethyldisilazide, 2.) BF3*Et2O / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h 2: MsCl, Et3N / CH2Cl2 / 48 h / Ambient temperature 3: H2 / PtO2 / ethyl acetate / 4 h / 760 Torr / Ambient temperature 4: 6 N HCl / Heating View Scheme

1.1: lithium triethylborohydride / toluene / -70 - -60 °C 2.1: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 3.1: water; lithium hydroxide hydrate / ethanol 4.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 5.1: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C 6.1: isopropyl alcohol / 60 °C 7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 8.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 8.2: 18 h / 20 °C View Scheme

1: lithium triethylborohydride / toluene / -70 - -60 °C 2: 4-(N,N-dimethlyamino)pyridine; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine 3: water; lithium hydroxide hydrate / ethanol 4: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran 5: diethylzinc / ethylene glycol dimethyl ether; dichloromethane / -30 - 20 °C 6: isopropyl alcohol / 60 °C View Scheme

1: 83 percent / tetrahydrofuran / -40 °C 2: 93 percent / TFA / CH2Cl2 3: 1.) DDQ; 2.) 10percent NaOH / 1.) CH2Cl2, rt., 1 h; 2.) reflux, 12 h View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 2 h / -78 °C 2.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C 3.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C 5.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice 5.2: 16 h / 20 °C 6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7.1: tetraethyl ammonium fluoride / tetrahydrofuran / 16 h / Reflux 8.1: water; acetic acid / 1.5 h / Heating 9.1: pyridine / dichloromethane / 16 h / 20 °C 10.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C / Inert atmosphere View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 2 h / -78 °C 2.1: sodium tetrahydroborate / methanol; water / 1 h / 20 °C 3.1: toluene-4-sulfonic acid / acetone / 1 h / -20 - 20 °C 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 16 h / 20 °C 5.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / Cooling with ice 5.2: 16 h / 20 °C 6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7.1: tetraethyl ammonium fluoride / tetrahydrofuran / 16 h / Reflux 8.1: water; acetic acid / 1.5 h / Heating 9.1: pyridine / dichloromethane / 16 h / 20 °C 10.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 80 °C / Inert atmosphere 11.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 11.2: 12 h / -78 - 0 °C View Scheme