1: sodium hydride / paraffin oil / 90 °C / |Inert atmosphere 2: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / |Inert atmosphere 3: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 4: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 5: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 6: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 7: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 8: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 9: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / |Inert atmosphere 2: AlCl3, aluminium chloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 3: sodium hydride / paraffin oil / 90 °C / |Inert atmosphere 4: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / |Inert atmosphere 5: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 6: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 7: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 8: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 9: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 10: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 11: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: AlCl3, aluminium chloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 2: sodium hydride / paraffin oil / 90 °C / |Inert atmosphere 3: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / |Inert atmosphere 4: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 5: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 6: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 7: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 8: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 9: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 10: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 2: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 4: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 5: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 6: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 7: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: sodium tetrahydroborate / methanol / 1 h / 0 - 20 °C / |Inert atmosphere 2: pyridinium p-toluenesulfonate / toluene / |Inert atmosphere; |Reflux; |Dean-Stark 3: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 5: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 6: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 7: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 8: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / |Inert atmosphere 2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 3: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 4: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 5: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 6: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1.5 h / -78 - 20 °C / |Inert atmosphere 2: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 3: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 4: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 5: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: AD-mix-βreg;; methanesulfonamide; osmium(VIII) oxide / dichloromethane; #tert!-butyl alcohol; water / 72 h / 20 °C / |Inert atmosphere 2: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 3: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 4: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: pyridinium p-toluenesulfonate / toluene / 2 h / 90 °C / |Inert atmosphere 2: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 3: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme

1: lithium hydroxide hydrate / methanol; tetrahydrofuran / 0.5 h / 20 °C / |Inert atmosphere 2: boron tribromide / dichloromethane / -78 - 20 °C / |Inert atmosphere View Scheme