potassium tert-butylate; hydrogen; [tris(.mu.-chloro)bis((triphos)ruthenium(II))] chloride in methanol T=100°C; P=30003 Torr; 16 h; Inert atmosphereAutoclave;

in acetonitrile T=20°C; Condensation;

sodium hydroxide in tetrahydrofuran; dichloromethane

1: With triethylamine in tetrahydrofuran T=0°C; 1 h; 2: With sodium tetrahydroborate in tetrahydrofuran; water T=0 - 20°C;

1: 2-azido-3-phenylpropan-1-ol With trimethylphosphane in tetrahydrofuran T=20°C; 2 h; 2: di-tert-butyl dicarbonate With sodium hydroxide in tetrahydrofuran

1: 45 percent / Et3N, diphenylphosphoryl azide / toluene / 7 h / Heating 2: 77 percent / 48 h / Heating 3: 1.) O3; 2.) NaBH4 / 1.) CH2Cl2, -15 deg C, 8 min; 2.) EtOH, 0 deg C, 1.5 h View Scheme

1: 88 percent / KOH / methanol / 16 h / Ambient temperature 2: 45 percent / Et3N, diphenylphosphoryl azide / toluene / 7 h / Heating 3: 77 percent / 48 h / Heating 4: 1.) O3; 2.) NaBH4 / 1.) CH2Cl2, -15 deg C, 8 min; 2.) EtOH, 0 deg C, 1.5 h View Scheme

1: 68.2 g / di-isobutylaluminium hydride / hexane / 0.5 h / -60 °C 2: 1.) butyl-lithium / 1.) THF, hexane, 30 min, -60 deg C; 2.) THF, RT, 1 h 3: 1.) borane*THF, cyclohexane; 2.) aq. KOH, H2O2 / 1.) THF, 2 h; 2.) MeOH, RT, 1.5 h 4: 82 percent / diethyl ether / Ambient temperature 5: 56 percent / lithium di-isopropylamide, HMPA / tetrahydrofuran 6: 88 percent / KOH / methanol / 16 h / Ambient temperature 7: 20 percent / Et3N, diphenylphosphoryl azide / toluene / 7 h / Heating 8: Heating 9: 1.) O3; 2.) NaBH4 / 1.) CH2Cl2, -15 deg C, 8 min; 2.) EtOH, 0 deg C, 1.5 h View Scheme

1: 1.) butyl-lithium / 1.) THF, hexane, 30 min, -60 deg C; 2.) THF, RT, 1 h 2: 1.) borane*THF, cyclohexane; 2.) aq. KOH, H2O2 / 1.) THF, 2 h; 2.) MeOH, RT, 1.5 h 3: 82 percent / diethyl ether / Ambient temperature 4: 56 percent / lithium di-isopropylamide, HMPA / tetrahydrofuran 5: 88 percent / KOH / methanol / 16 h / Ambient temperature 6: 20 percent / Et3N, diphenylphosphoryl azide / toluene / 7 h / Heating 7: Heating 8: 1.) O3; 2.) NaBH4 / 1.) CH2Cl2, -15 deg C, 8 min; 2.) EtOH, 0 deg C, 1.5 h View Scheme

1: 56 percent / lithium di-isopropylamide, HMPA / tetrahydrofuran 2: 88 percent / KOH / methanol / 16 h / Ambient temperature 3: 45 percent / Et3N, diphenylphosphoryl azide / toluene / 7 h / Heating 4: 77 percent / 48 h / Heating 5: 1.) O3; 2.) NaBH4 / 1.) CH2Cl2, -15 deg C, 8 min; 2.) EtOH, 0 deg C, 1.5 h View Scheme