1.1: 100 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 5 h / 20 °C 2.1: 89 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C 3.1: 87 percent / DIBAL-H / toluene / 1 h / -78 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 50 °C 4.2: 53 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C 5.1: NaH; imidazole / tetrahydrofuran / 0.5 h / 20 °C 5.2: tetrahydrofuran / 2 h / 60 °C 5.3: 99 percent / tetrahydrofuran / 1 h / 0 - 20 °C 6.1: 91 percent / n-Bu3SnH; AIBN / benzene / 2 h / 80 °C 7.1: 49 percent / HCl / methanol / 0.5 h / 40 °C 8.1: 50 percent / Ph3P; DEAD / tetrahydrofuran / 1.5 h / 20 °C View Scheme

sodium hydride in N,N-dimethyl-formamide T=20°C; 1 h;

1: 96 percent / cc. H2SO4 / 8 h / Heating 2: 1.) sodium hydride (NaH) / 1.) tetrahydrofuran (THF), 0 deg C to room temp., 1 h; 2.) THF, 0 deg C to room temp., 8 h View Scheme

1: 78 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / -10 °C 2: 84 percent / tert-butyl hydroperoxide (70percent), vanadyl acetylacetonate / H2O; CH2Cl2 / 6 h / Ambient temperature 3: 81 percent / aq. sodium hydroxide (1percent) / 2.5 h / 70 °C 4: 72 percent / CH2Cl2; pyridine / 6 h / -10 °C 5: 99 percent / potassium carbonate (K2CO3) / methanol / 0.5 h / Ambient temperature 6: 95 percent / H2 / Pd-C (5percent) / ethyl acetate 7: 86 percent / potassium carbonate (K2CO3) / methanol / 0.5 h / Ambient temperature 8: 1.) sodium hydride (NaH) / 1.) THF, 0 deg C, 1 h; 2.) THF, room temp., 1 h 9: 76 percent / HCl (2N) / methanol / 2 h / Ambient temperature View Scheme