1: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C 2: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C 3: triethylamine / toluene / 2 h / 23 °C 4: 86 percent / sodium methoxide / toluene; methanol / 14 h / 80 - 110 °C 5: 99 percent / HCl / propan-2-ol / 5 h / 75 °C View Scheme

1: (S,S)-[(salen)Al]2O; t-BuOH / cyclohexane / 54 h / 20 °C 2: 86 percent / Raney nickel / toluene; methanol / 14 h / 75 °C / 33614.6 Torr 3: sodium methoxide / toluene; methanol / 1 h / 75 °C 4: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C 5: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C 6: triethylamine / toluene / 2 h / 23 °C 7: 86 percent / sodium methoxide / toluene; methanol / 14 h / 80 - 110 °C 8: 99 percent / HCl / propan-2-ol / 5 h / 75 °C View Scheme

1: sodium methoxide / toluene; methanol / 1 h / 75 °C 2: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C 3: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C 4: triethylamine / toluene / 2 h / 23 °C 5: 86 percent / sodium methoxide / toluene; methanol / 14 h / 80 - 110 °C 6: 99 percent / HCl / propan-2-ol / 5 h / 75 °C View Scheme

1: 86 percent / Raney nickel / toluene; methanol / 14 h / 75 °C / 33614.6 Torr 2: sodium methoxide / toluene; methanol / 1 h / 75 °C 3: lithium aluminum hydride / tetrahydrofuran; toluene / 5 h / 75 °C 4: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C 5: triethylamine / toluene / 2 h / 23 °C 6: 86 percent / sodium methoxide / toluene; methanol / 14 h / 80 - 110 °C 7: 99 percent / HCl / propan-2-ol / 5 h / 75 °C View Scheme

1.1: 97 percent / triethylamine / CH2Cl2 / 3 h / 20 °C 2.1: sodium hydroxide / xylene; butan-2-ol / 10 h / Heating 2.2: 78.5 percent / aq. HCl / propan-2-ol / pH 2 3.1: 89.5 percent / H2 / Pd/C / propan-2-ol / 3 h / 40 °C / 375.03 - 3750.3 Torr View Scheme

1.1: sodium hydroxide / xylene; butan-2-ol / 10 h / Heating 1.2: 78.5 percent / aq. HCl / propan-2-ol / pH 2 2.1: 89.5 percent / H2 / Pd/C / propan-2-ol / 3 h / 40 °C / 375.03 - 3750.3 Torr View Scheme

potassium hydroxide in water; ethylene glycol T=100°C; 20 h;

1.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C 2.1: magnesium / tetrahydrofuran / 25 °C 2.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C 2.3: tetrahydrofuran / 0.67 h / -50 - 0 °C 3.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C 4.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 5.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 6.1: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme

1.1: 95 percent / borane dimethyl sulfide complex / (S)-2-methyl-CBS-oxazaborolidine catalyst / CH2Cl2; tetrahydrofuran; toluene / 2 h / -20 °C 2.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C 3.1: magnesium / tetrahydrofuran / 25 °C 3.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C 3.3: tetrahydrofuran / 0.67 h / -50 - 0 °C 4.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C 5.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 6.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 7.1: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme

1.1: 86 percent / CH2Cl2 / 18 h / 25 °C 2.1: 95 percent / borane dimethyl sulfide complex / (S)-2-methyl-CBS-oxazaborolidine catalyst / CH2Cl2; tetrahydrofuran; toluene / 2 h / -20 °C 3.1: 89 percent / pyridine; DMAP / CH2Cl2 / 2 h / 25 °C 4.1: magnesium / tetrahydrofuran / 25 °C 4.2: CuCN / tetrahydrofuran / 0.67 h / -18 °C 4.3: tetrahydrofuran / 0.67 h / -50 - 0 °C 5.1: potassium fluoride; hydrogen peroxide / dimethylformamide; H2O / 18 h / 25 °C 6.1: hydrogen / [Ir(COD)(PCy3)Pyr]PF6 / CH2Cl2 / 20 h / 25 °C / 760 Torr 7.1: PPh3; DIAD / tetrahydrofuran / 2 h / 50 °C 8.1: KOH / ethane-1,2-diol; H2O / 20 h / 100 °C View Scheme