1: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1.1: hydrogenchloride; methanol; zinc / 1 h / 0 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere 2.2: 0.25 h / Inert atmosphere 3.1: boron trifluoride diethyl etherate / acetone / 1 h / 0 °C / Inert atmosphere 4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 5.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-tartaric acid diethyl ester / decane; dichloromethane / 69 h / -20 °C / Inert atmosphere 6.1: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 8.1: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 9.1: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 10.1: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 11.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 12.1: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 13.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 14.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 15.1: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 16.1: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 17.1: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 18.1: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 19.1: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 20.1: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 21.1: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 22.1: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 23.1: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 24.1: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 25.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: boron trifluoride diethyl etherate / acetone / 1 h / 0 °C / Inert atmosphere 2: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 3: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-tartaric acid diethyl ester / decane; dichloromethane / 69 h / -20 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 6: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 7: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 8: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 9: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 10: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 11: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 12: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 13: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 14: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 15: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 16: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 17: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 18: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 19: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 20: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 21: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 22: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 23: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-tartaric acid diethyl ester / decane; dichloromethane / 69 h / -20 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 5: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 6: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 7: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 8: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 9: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 10: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 11: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 12: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 13: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 14: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 15: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 16: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 17: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 18: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 19: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 20: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 21: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 22: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-tartaric acid diethyl ester / decane; dichloromethane / 69 h / -20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 4: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 5: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 6: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 7: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 8: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 9: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 10: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 11: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 12: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 13: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 14: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 15: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 16: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 17: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 18: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 19: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 20: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 21: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 4: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 5: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 6: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 7: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 8: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 9: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 10: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 11: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 12: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 13: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 14: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 15: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 16: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 17: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 18: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 19: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 20: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 3: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 4: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 6: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 7: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 8: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 9: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 10: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 11: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 12: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 13: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 14: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 15: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 16: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 17: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 18: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 19: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 2: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 3: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 5: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 6: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 7: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 8: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 9: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 10: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 11: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 12: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 13: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 14: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 15: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 16: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 17: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 18: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 3: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 4: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 6: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 7: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 8: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 9: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 10: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 11: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 12: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 13: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 14: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 15: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 16: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme

1: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 2: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 3: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere 4: hydrogen / ethanol / 15 h / 20 °C / 760.05 Torr / Inert atmosphere 5: tetrahydrofuran / 29 h / 50 °C / Inert atmosphere 6: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere 7: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C / Inert atmosphere View Scheme