1: 1.) LiAlH4, 2.) NaIO4 / 1.) Et2O, reflux, 2 h, 2.) THF, H2O, room temperature, 2 h 2: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) room temperature, overnight 3: m-CPBA, NaHCO3 / hexane; H2O / 2 h / Ambient temperature 4: 1.) Na(PhSe)BH3, 2.) 30percent H2O2, pyridine / 1.) EtOH, reflux, 2 h, 2.) THF, 0 deg C, overnignt; room temperature, 3 h 5: 1.) O3, pyridine, 2.) NaBH4 / 1.) MeOH, -78 deg C, 2.) room temperature, 36 h 6: 62 percent / Jones' reagent / acetone / 0.5 h 7: 70 percent / H2 / 5percent Pd-C / ethanol View Scheme

1: triethylamine and 4-(N,N-dimethyl amino)-pyridine / CH2Cl2 2: 1.) aq.HClO4; 2.) K2CO3 / 1.) in DMF, room temperature, 8h; in anhydrous methanol 3: triethylamine / CH2Cl2 / 0 °C 4: sodium naphthalide / tetrahydrofuran View Scheme

1: 84 percent / CBr4; triphenylphosphine / CH2Cl2 / 0 °C 2: BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C View Scheme

1H-imidazole; 2,6-dimethylpyridine; water; iodine; triphenylphosphine in 1,2-dichloro-ethane; benzene T=75 - 80°C; 2 h; stereospecific 1,3-transposition of various chiral 2,3-epoxy alcohols; Mechanism;

1H-imidazole; iodine; triphenylphosphine in benzene T=75 - 80°C; 4 h; stereospecific 1,3-transposition of various chiral 2,3-epoxy alcohols; Product distribution;

sodium bis(2-methoxyethoxy)aluminium dihydride in tetrahydrofuran T=0°C; 5 h; Title compound not separated from byproducts;

1: Ph3P; I2; pyridine / diethyl ether; acetonitrile / 2 h / 0 °C 2: H2O / diethyl ether; acetonitrile / 10 h / 38 °C 3: 70 percent / Et3N; DMAP / 10 h / 20 °C View Scheme