1: DMAP, Et3N / dimethylformamide / 48 h / Ambient temperature 2: 1.) NaH / 1.) THF, 24 h, 2.) THF, 2 d 3: TsOH / methanol / 8 h / 80 °C 4: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 45 min, 2.)CH2Cl2, 0 deg C, overnight View Scheme

1: 1.) NaH / 1.) THF, 24 h, 2.) THF, 2 d 2: TsOH / methanol / 8 h / 80 °C 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 45 min, 2.)CH2Cl2, 0 deg C, overnight View Scheme

1: 1.) NaH / 1.) THF, 24 h, 2.) THF, 2 d 2: TsOH / methanol / 8 h / 80 °C 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 45 min, 2.)CH2Cl2, 0 deg C, overnight View Scheme

1: TsOH / methanol / 8 h / 80 °C 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 45 min, 2.)CH2Cl2, 0 deg C, overnight View Scheme

oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) CH2Cl2, -78 deg C, 45 min, 2.)CH2Cl2, 0 deg C, overnight; Yield given. Multistep reaction;

1: tetrahydrofuran / 0.25 h 2: 1.) NaH / 1.) THF, 0 deg C, 1 h, 2.) reflux, 12-20 h 3: 1.) ozone, 2.) dimethyl sulfide / 1.) dichloromethane, -78 deg C, 2.) -78 deg C to room temperature, 2-3 h, then room temperature, 12 h View Scheme

1.1: sodium hydroxide; potassium permanganate / water / 16.5 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 1.2: |Cooling; |Inert atmosphere; |Schlenk technique 2.1: sodium hydroxide; sodium tetrahydroborate / water / 16.5 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 2.2: |Inert atmosphere; |Schlenk technique 3.1: acetyl chloride / 4 h / 65 °C / |Inert atmosphere; |Schlenk technique 4.1: sodium hydride / mineral oil; tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / 0 °C / |Inert atmosphere; |Schlenk technique 4.2: 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 5.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / |Inert atmosphere; |Schlenk technique 6.2: 1 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique View Scheme

1.1: sodium hydroxide; sodium tetrahydroborate / water / 16.5 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 1.2: |Inert atmosphere; |Schlenk technique 2.1: acetyl chloride / 4 h / 65 °C / |Inert atmosphere; |Schlenk technique 3.1: sodium hydride / mineral oil; tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / 0 °C / |Inert atmosphere; |Schlenk technique 3.2: 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 4.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / |Inert atmosphere; |Schlenk technique 5.2: 1 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique View Scheme

1.1: acetyl chloride / 4 h / 65 °C / |Inert atmosphere; |Schlenk technique 2.1: sodium hydride / mineral oil; tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / 0 °C / |Inert atmosphere; |Schlenk technique 2.2: 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 3.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / |Inert atmosphere; |Schlenk technique 4.2: 1 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique View Scheme

1.1: sodium hydride / mineral oil; tetrahydrofuran; N,N-dimethyl-formamide / 0.33 h / 0 °C / |Inert atmosphere; |Schlenk technique 1.2: 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 2.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / |Inert atmosphere; |Schlenk technique 3.2: 1 h / -78 - 20 °C / |Inert atmosphere; |Schlenk technique View Scheme