1: With titanium(IV) isopropylate; L-(+)-DIPT in dichloromethane T=-35°C; Sharpless epoxidation; 0.5 h; Molecular sieveInert atmosphere; 2: With alpha,alpha-dimethylbenzyl hydroperoxide in dichloromethane T=-25°C; Sharpless epoxidation; 20 h; Inert atmosphere; optical yield given as percent ee;

sodium tetrahydroborate in methanol T=20°C; 0.5 h;

1: 72 percent / Et3N / CH2Cl2 / 15 h / 20 °C 2: 96 percent / NaBH4; CeCl3*7H2O / methanol / 2 h / 20 °C 3: 82 percent / CaH2; titanium tetraisopropoxide; tert-butyl hydroperoxide / L-(+)-diisopropyltartrate; molecular sieves 3 Angstroem / CH2Cl2 / 48 h / -20 °C View Scheme

1: 96 percent / NaBH4; CeCl3*7H2O / methanol / 2 h / 20 °C 2: 82 percent / CaH2; titanium tetraisopropoxide; tert-butyl hydroperoxide / L-(+)-diisopropyltartrate; molecular sieves 3 Angstroem / CH2Cl2 / 48 h / -20 °C View Scheme

1.1: aq. NaOH; cetyltrimethylammonium chloride / 1,2-dichloro-ethane / 5 h / 80 °C 2.1: 48 mg / p-TsOH / 12 h / 80 °C 3.1: 86 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.33 h / -78 °C 4.1: n-BuLi / diethyl ether; hexane / 0.08 h / 0 °C 4.2: 62 percent / diethyl ether; hexane / 0.17 h / 0 °C 5.1: 83 percent / H2 / Pd/C / ethanol / 2.5 h 6.1: 89 percent / HCl / methanol / 7 h / 20 °C 7.1: 77 percent / K2CO3 / methanol / 0.33 h / 20 °C 8.1: 84 percent / NaBH4 / methanol / 0.5 h / 20 °C View Scheme

1.1: n-BuLi / diethyl ether; hexane / 0.08 h / 0 °C 1.2: 62 percent / diethyl ether; hexane / 0.17 h / 0 °C 2.1: 83 percent / H2 / Pd/C / ethanol / 2.5 h 3.1: 89 percent / HCl / methanol / 7 h / 20 °C 4.1: 77 percent / K2CO3 / methanol / 0.33 h / 20 °C 5.1: 84 percent / NaBH4 / methanol / 0.5 h / 20 °C View Scheme

1.1: 86 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.33 h / -78 °C 2.1: n-BuLi / diethyl ether; hexane / 0.08 h / 0 °C 2.2: 62 percent / diethyl ether; hexane / 0.17 h / 0 °C 3.1: 83 percent / H2 / Pd/C / ethanol / 2.5 h 4.1: 89 percent / HCl / methanol / 7 h / 20 °C 5.1: 77 percent / K2CO3 / methanol / 0.33 h / 20 °C 6.1: 84 percent / NaBH4 / methanol / 0.5 h / 20 °C View Scheme

1: 83 percent / H2 / Pd/C / ethanol / 2.5 h 2: 89 percent / HCl / methanol / 7 h / 20 °C 3: 77 percent / K2CO3 / methanol / 0.33 h / 20 °C 4: 84 percent / NaBH4 / methanol / 0.5 h / 20 °C View Scheme

1.1: hydrogen; sodium hydride / tetrahydrofuran / 24 h / Inert atmosphere; Reflux 2.1: potassium carbonate / water / 80 °C 3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.67 h / -30 °C / Inert atmosphere 4.1: titanium(IV) isopropylate; L-(+)-DIPT / dichloromethane / 0.5 h / -35 °C / Molecular sieve; Inert atmosphere 4.2: 20 h / -25 °C / Inert atmosphere View Scheme

1.1: potassium carbonate / water / 80 °C 2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.67 h / -30 °C / Inert atmosphere 3.1: titanium(IV) isopropylate; L-(+)-DIPT / dichloromethane / 0.5 h / -35 °C / Molecular sieve; Inert atmosphere 3.2: 20 h / -25 °C / Inert atmosphere View Scheme