1: 1.) CuI, THF-Me2S / 1.) THF, -78 deg C, 2.) -78 deg C 2: 1.) NaH / 1.) THF, DMF, RT, 2.) RT 3: 1.) borane-THF complex, 2.) 30percent H2O2, 3N NaOH / 1.) THF, 45 deg C, 2.) 60 deg C 4: 1.) NEt3, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) CH2Cl2, RT, 16h, 2.) EtOH, MeOH, 1 atm, RT, 6h View Scheme

1.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 1.2: 89 percent / toluene; tetrahydrofuran / 12 h / -78 °C 2.1: 76 percent / NMO; aq. OsO4 / dioxane; 2-methyl-propan-2-ol / 24 h / 60 °C 3.1: 96 percent / H2; aq. HCl / Pd(OH)2 / methanol / 24 h / 2280 Torr View Scheme