1: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h 2: 90 percent / pyridine / pyridine / 48 h / 23 °C 3: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C 4: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 5: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate in water; N,N-dimethyl-formamide T=20°C;

chromium(VI) oxide; sulfuric acid in acetone T=0°C; 1 h;

Na2B4O7 in methanol

1: AlCl3 / CH2Cl2 / 2.5 h / 0 °C 2: Na2B4O7 / methanol; H2O / 0.5 h View Scheme

1: With n-butyllithium Inert atmosphere; 2: With potassium carbonate in methanol Inert atmosphere;

1: 1.) ethylmagnesium bromide / 1.) THF, 2.) THF, 23 deg C, 16 h 2: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C View Scheme

ammonia in dichloromethane

2: borax / methanol View Scheme

1: 74 percent / NaN3; AlCl3 / tetrahydrofuran / 216 h / Heating 2: 69 percent / Pb(OAc)4 / dioxane / 0.33 h / 10 - 15 °C View Scheme