1: tetrahydrofuran / 0 - 22 °C 2: thionyl chloride / tetrahydrofuran / 12 h / 22 °C 3: acetonitrile / 8 h / 60 °C 4: hydrogen bromide / water; acetic acid / 4 h / 112 °C 5: Rh(COD)[(S,S)-Me-DPEphos]BF4; hydrogen; lithium tert-butylate / toluene / 2 h / 20 °C / 2585.81 Torr / Inert atmosphere View Scheme

1: With lithium aluminium tetrahydride in diethyl ether 96 h; Heating / reflux; 2: With acetic acid in diethyl ether pH=5; Product distribution / selectivity;

lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal 1) ether, rt, overnight; 2) MeOH, 1 atm, rt, overnight; Yield given. Multistep reaction;

1: 1.) SOCl2 / 1) benzene, 50 deg C, 50 min; 2) ether, rt, 1.5 h 2: 1.) LiAlH4, 2.) H2 / 2.) Pd/C / 1) ether, rt, overnight; 2) MeOH, 1 atm, rt, overnight View Scheme

1.1: |Inert atmosphere; |Schlenk technique 2.1: triethylamine / toluene / 2 h / 150 °C / |Inert atmosphere 3.1: sec.-butyllithium / diethyl ether; cyclohexane; hexane / 1 h / -78 °C / |Inert atmosphere; |Schlenk technique 3.2: 2 h / -78 °C / |Inert atmosphere; |Schlenk technique 3.3: 16.08 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique 4.1: tetrabutyl ammonium fluoride; water / toluene / 1.5 h / 20 °C 5.1: osmium(VIII) oxide; sodium periodate 6.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 7.1: hydrogen bromide; acetic acid View Scheme

1.1: triethylamine / toluene / 2 h / 150 °C / |Inert atmosphere 2.1: sec.-butyllithium / diethyl ether; cyclohexane; hexane / 1 h / -78 °C / |Inert atmosphere; |Schlenk technique 2.2: 2 h / -78 °C / |Inert atmosphere; |Schlenk technique 2.3: 16.08 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique 3.1: tetrabutyl ammonium fluoride; water / toluene / 1.5 h / 20 °C 4.1: osmium(VIII) oxide; sodium periodate 5.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 6.1: hydrogen bromide; acetic acid View Scheme

1.1: sec.-butyllithium / diethyl ether; cyclohexane; hexane / 1 h / -78 °C / |Inert atmosphere; |Schlenk technique 1.2: 2 h / -78 °C / |Inert atmosphere; |Schlenk technique 1.3: 16.08 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique 2.1: tetrabutyl ammonium fluoride; water / toluene / 1.5 h / 20 °C 3.1: osmium(VIII) oxide; sodium periodate 4.1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 5.1: hydrogen bromide; acetic acid View Scheme

1: tetrabutyl ammonium fluoride; water / toluene / 1.5 h / 20 °C 2: osmium(VIII) oxide; sodium periodate 3: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 4: hydrogen bromide; acetic acid View Scheme

1: osmium(VIII) oxide; sodium periodate 2: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 3: hydrogen bromide; acetic acid View Scheme

1: sodium tris(acetoxy)borohydride / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 2: hydrogen bromide; acetic acid View Scheme