1: 57 percent / 3-chloroperoxybenzoic acid / CHCl3; ethanol / 2 h / Heating 2: 60 percent / Et2N-COCl / dioxane / 16 h / 80 °C View Scheme

1: 25 percent / 3-chloroperoxybenzoic acid / CHCl3; ethanol / 2 h / Heating 2: 50 percent / Et2N-COCl / dioxane / 16 h / 80 °C View Scheme

1: 74 percent / 50percent NaH / dimethylformamide 2: 48 percent / DDQ / benzene / 0.75 h / Heating View Scheme

1: 1) n-BuLi / 1) THF, hexane, -75 deg C, 1.5 h, 2) THF, -75 deg C, 1 h 2: 78 percent / pyridinium chloride / 0.25 h / 210 °C View Scheme

1: 94 percent / Br2 / tetrahydrofuran / 1 h 2: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h 3: 50 percent / 70percent HClO4 / tetrahydrofuran; H2O / 3 h / Ambient temperature 4: 62 percent / borane-trimethylamine / acetic acid; tetrahydrofuran / 1 h / 0 °C 5: 1.) 5.25percent NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

1: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h 2: 74 percent / 17.5percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature 3: 75 percent / borane-trimethylamine / tetrahydrofuran; acetic acid / 1 h / 0 °C 4: 1.) aq. NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme