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 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: H2 / PtO2 / ethyl acetate / 4 h / 760 Torr / Ambient temperature 2: 6 N HCl / Heating View Scheme

trifluoroacetic acid in dichloromethane T=0°C; Yield given;

1: PTSA / Ambient temperature 2: 1N aq. NaOH / tetrahydrofuran / 0 °C 3: 0 °C / Jones oxidation 4: TFA / CH2Cl2 / 0 °C View Scheme

hydrogenchloride Heating;