1: sodium methoxide / Heating 2: methanol / Dowex 50W-X8 resin (H+ form) / Heating 3: pyridine / CH2Cl2 / 0.33 h / -20 °C 4: NaN3 / dimethylformamide / 48 h / 50 °C 5: methanol / sodium methylate / Ambient temperature 6: pyridine / 6 h / Ambient temperature 8: pyridine / -20 °C 9: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran 10: H2O / CF3COOH / 1 h / Ambient temperature 11: NaBH4 / ethanol; H2O 12: H2 / palladium hydroxide / ethanol View Scheme

1: 89 percent / imidazole / CH2Cl2 / 1.5 h / 0 °C 2: 90 percent / Et3N / CH2Cl2 / 1 h / cooling 3: 55 percent / NaN3 / dimethylformamide / 20 h / 120 °C 4: 80 percent / Bu4NF / tetrahydrofuran / 24 h / 20 °C 5: 68 percent / aq. PPh3 / tetrahydrofuran / 24 h / 20 °C 6: 62 percent / NaHCO3 / methanol / 3 h / 20 °C 7: 89 percent / aq. TFA / 5 h / 20 °C 8: 45 percent / H2 / Pd/C / methanol / 24 h 9: H2 / Pd(OH)2/C / methanol / 24 h View Scheme

1: sodium periodate / tetrahydrofuran; H2O / 2 h / 0 °C 2: 30.39 g / NaOH / dioxane; H2O / 42 h / 20 °C View Scheme

barium dihydroxide; BaO in N,N-dimethyl-formamide 2 h; Ambient temperature;

sodium hydride in N,N-dimethyl-formamide 3 h; Ambient temperature;

sodium hydroxide; tetrabutylammomium bromide 0.666667 h; Ambient temperature;

sodium hydride 1.) DMF, 0 deg C, 2.) DMF, RT, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

1: sodium methoxide / 3 h / Heating 2: acid resin (Dowex 50W-XH) / methanol / 12 h / Heating 3: pyridine / CH2Cl2; pyridine / 0.25 h / -30 °C 4: sodium azide / dimethylformamide / 24 h / 50 °C 5: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature 6: 81 percent / pyridine / 4 h / from 0 deg C to room temp. 7: 94 percent / pyridine / 4 h / Ambient temperature 8: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 9: sodium methoxide / dimethylformamide / 3 h / 50 °C 10: hydrogen / palladium black / ethanol / 1 h 11: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 12: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 13: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme

1H-imidazole; iodine; chloro-diphenylphosphine; zinc 1) toluene, reflux, 30 min, 2) reflux, 30 min; Yield given. Multistep reaction;

1: sodium methoxide / Heating 2: methanol / Dowex 50W-X8 resin (H+ form) / Heating 3: pyridine / CH2Cl2 / 0.33 h / -20 °C 4: NaN3 / dimethylformamide / 48 h / 50 °C 5: methanol / sodium methylate / Ambient temperature 6: pyridine / 0 °C 7: pyridine / 4 h / Ambient temperature 8: sodium methoxyde / dimethylformamide / 5 h / 50 °C 10: H2O / CF3COOH / Ambient temperature 11: NaBH4 / ethanol; H2O 12: H2 / palladium hydroxide / ethanol View Scheme