1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 1 h / -40 °C / |Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / |Reflux; |Dean-Stark 3.1: hydrogen; palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: HLAP; water / aq. buffer / 48 h / 40 °C / pH 7.5 / |Enzymatic reaction View Scheme

1: NaBH4 / ethanol 2: PBr3 / CH2Cl2 3: 76 percent / LiHMDS / tetrahydrofuran 4: 81 percent / LiOH; H2O2 5: 95 percent / LAH / tetrahydrofuran 6: 97 percent / PPh3; NBS / CH2Cl2 7: 68 percent / n-BuLi 8: HCl / acetonitrile 9: Et3N 10: NaBH4 / ethanol 11: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2 12: Mg 13: 23 percent / H2 / Pd(OH)2/C 14: 38 percent / TPAP; NMMO View Scheme

1.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C 2.1: 100 percent / Me3SiBr / 0.17 h / 20 °C 3.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C 3.2: 86 percent / tetrahydrofuran / 18 h / 0 °C 4.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C 5.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C 5.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C 6.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C 7.1: BuLi / hexane / 0.5 h / -75 °C 7.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C 8.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C 9.1: 82 percent / Et3N / CH2Cl2 / 20 h / 20 °C View Scheme

1.1: lithium diisopropyl amide / n-heptane; benzene; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 1.2: 2.25 h / -40 °C 2.1: camphor-10-sulfonic acid / toluene / Dean-Stark system; Reflux 3.1: hydrogen / palladium 10 on activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: hydrogenchloride; tri-(hydroxymethyl)-methylamine; water; HLAP / 48 h / 40 °C / Enzymatic reaction 4.2: 20 °C / pH 3.5 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 40 °C / Inert atmosphere 5.2: 20 °C 6.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere 7.1: sodium iodide / acetonitrile / Inert atmosphere; Reflux View Scheme