1: With sodium tetrahydroborate; water 2: With sodium periodate; silica gel regioselective reaction;

{Rh[(R)-BINAP](COD)}ClO4 in tetrahydrofuran T=70°C; 24 h; Inert atmosphere; optical yield given as percent ee;

1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-78°C; Swern Oxidation; 0.666667 h; 2: With triethylamine in dichloromethane T=-78°C; Swern Oxidation;

1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 2: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 3: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 4: sodium tetrahydroborate; water / Inert atmosphere View Scheme

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere 1.2: 18 h / -78 - 20 °C / Inert atmosphere 2.1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 3.1: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 4.1: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 5.1: sodium tetrahydroborate; water / Inert atmosphere View Scheme

1.1: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere 1.2: 0.67 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere 3.2: 18 h / -78 - 20 °C / Inert atmosphere 4.1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 5.1: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 6.1: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 7.1: sodium tetrahydroborate; water / Inert atmosphere View Scheme

1.1: acetic acid / 1 h / Reflux; Inert atmosphere 1.2: 0.5 h / 50 °C / Inert atmosphere 1.3: 1 h / 50 - 60 °C 2.1: sulfuric acid / ethanol / 0.25 h / 5 °C / Inert atmosphere 2.2: 1.5 h 2.3: 4 h / Reflux 3.1: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere 3.2: 0.67 h / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere 5.2: 18 h / -78 - 20 °C / Inert atmosphere 6.1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 7.1: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 8.1: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 9.1: sodium tetrahydroborate; water / Inert atmosphere View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere 2.2: 18 h / -78 - 20 °C / Inert atmosphere 3.1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 4.1: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 5.1: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 6.1: sodium tetrahydroborate; water / Inert atmosphere View Scheme

1.1: sulfuric acid / ethanol / 0.25 h / 5 °C / Inert atmosphere 1.2: 1.5 h 1.3: 4 h / Reflux 2.1: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere 2.2: 0.67 h / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere 4.2: 18 h / -78 - 20 °C / Inert atmosphere 5.1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 6.1: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 7.1: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 8.1: sodium tetrahydroborate; water / Inert atmosphere View Scheme

1.1: cupric trifluoroacetate; (R)-BINOL-mono-PHOS / tetrahydrofuran; toluene / 7 h / 20 °C 2.1: lithium borohydride / tetrahydrofuran / 1 h / 0 - 20 °C 2.2: 4 h / 20 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.67 h / -78 °C 3.2: -78 °C View Scheme