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: 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 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 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 View Scheme