1: 1) KHMDS, 2) Et3N / 1) THF, -78 deg C, 60 min, 2) -78 deg C, 45 minalp 2: MCPBA / hexane / 0.5 h / Ambient temperature 3: aq. HF / acetonitrile / 0.33 h / Ambient temperature 4: NaIO4 / H2O; methanol / 1 h / Ambient temperature View Scheme

1: 1) KHMDS, 2) Et3N / 1) THF, -78 deg C, 60 min, 2) -78 deg C, 45 minalp 2: MCPBA / hexane / 0.5 h / Ambient temperature 3: aq. HF / acetonitrile / 0.33 h / Ambient temperature 4: NaIO4 / H2O; methanol / 1 h / Ambient temperature 5: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature 6: 1) 4-methylmorpholine / 1) DMF, r.t., 30 min, 2) THF, -10 deg C to r.t. 7: LiAlH4 / tetrahydrofuran / 0.25 h / -10 °C 8: 97 percent / TFA / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: 1) KHMDS, 2) Et3N / 1) THF, -78 deg C, 60 min, 2) -78 deg C, 45 minalp 2: MCPBA / hexane / 0.5 h / Ambient temperature 3: aq. HF / acetonitrile / 0.33 h / Ambient temperature 4: NaIO4 / H2O; methanol / 1 h / Ambient temperature 5: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature View Scheme

1: 1) KHMDS, 2) Et3N / 1) THF, -78 deg C, 60 min, 2) -78 deg C, 45 minalp 2: MCPBA / hexane / 0.5 h / Ambient temperature 3: aq. HF / acetonitrile / 0.33 h / Ambient temperature 4: NaIO4 / H2O; methanol / 1 h / Ambient temperature View Scheme

1: 1) KHMDS, 2) Et3N / 1) THF, -78 deg C, 60 min, 2) -78 deg C, 45 minalp 2: MCPBA / hexane / 0.5 h / Ambient temperature 3: aq. HF / acetonitrile / 0.33 h / Ambient temperature 4: NaIO4 / H2O; methanol / 1 h / Ambient temperature 5: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature 6: 1) 4-methylmorpholine / 1) DMF, r.t., 30 min, 2) THF, -10 deg C to r.t. View Scheme

hydrogenchloride in ethyl acetate 2 h; Ambient temperature;