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

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

1: 77 percent / 48 h / Heating 2: 1.) O3; 2.) NaBH4 / 1.) CH2Cl2, -15 deg C, 8 min; 2.) EtOH, 0 deg C, 1.5 h View Scheme

1: potassium hydrogencarbonate 2: lithium aluminium tetrahydride / 0 °C View Scheme

sodium tetrahydroborate; ozone 1.) CH2Cl2, -15 deg C, 8 min; 2.) EtOH, 0 deg C, 1.5 h; Yield given. Multistep reaction;

triethylamine in N,N-dimethylsulfoxide; dichloromethane

triethylamine in hexane; dichloromethane; dimethyl sulfoxide

Dess-Martin periodane T=0 - 20°C; 1 h;