1: BH3 / tetrahydrofuran / Ambient temperature 2: Ambient temperature View Scheme

1: 4N NaOH / 6 h / Ambient temperature 2: BH3.SMe2 / tetrahydrofuran / 10 h / 0 deg C to room temp. 3: pyridine.SO3 / dimethylsulfoxide / 0.5 h / 0 deg C to room temp. 4: benzene / 10 h / Ambient temperature 5: 1.) AD-mix-β / 1.) t-BuOH, water, 0 deg C - room temp.,24 h 6: water 7: H2, NaOAc / Pd/C / methanol / 12 h / 760 Torr View Scheme

1: 73 percent / HCl 2: 85 percent / conc. aq. NH3 3: 80 percent / NEt3 / CH2Cl2 4: 90 percent / LiAlH4 5: H2 / 10percent Pd-C / methanol View Scheme

1: 4N NaOH / 6 h / Ambient temperature 2: BH3.SMe2 / tetrahydrofuran / 10 h / 0 deg C to room temp. 3: pyridine.SO3 / dimethylsulfoxide / 0.5 h / 0 deg C to room temp. View Scheme

1: 4N NaOH / 6 h / Ambient temperature 2: BH3.SMe2 / tetrahydrofuran / 10 h / 0 deg C to room temp. View Scheme

thionyl chloride 8 h; Reflux;

1: 1) BF3*Et2O, BH3*Me2S, 2) aq. NaOH / 1) THF, reflux, 21 h, 2) THF, reflux, 4 h 2: NaOH / tetrahydrofuran; H2O / Ambient temperature 3: 96 percent / imidazole / dimethylformamide / Ambient temperature 4: 1) TMEDA, s-BuLi / 1) Et2O, cyclohexane, -78 deg C, 6 h, 2) Et2O, cyclohexane, -78 deg C -> room temperature, overnight 5: 93 percent / n-Bu4NF / tetrahydrofuran / 0 deg C, 1 h; room temperature, 2 h 6: 86 percent / N-methylmorpholine N-oxide, 4 Angstroem molecular sieves, (n-Pr)4NRuO4 / CH2Cl2 / Ambient temperature 7: 1) n-BuLi / 1) DME, hexane, -50 deg C, 30 min, 2) DME, hexane, -60 deg C, 2 h 8: 68 percent / sodium amalgam, disodium hydrogen phosphate / methanol / 3 h / Ambient temperature 9: 95 percent / Jones reagent / acetone / 0.5 h / Ambient temperature 10: 92 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature 11: 70 percent / NaBH3CN, AcOH / acetonitrile; H2O / 1.33 h / pH 7 View Scheme