1: SOCl2, pyridine / benzene / 1 h / Heating 2: 1.8548 g / benzoyl peroxide, N-bromosuccinimide / CCl4 / 0.67 h / Heating 3: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme

1: 92 percent / PBr3 / petroleum ether / 1 h / 0 °C 2: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme

1: KOH; ethanol / 4 h 2: nBu4NCN / 8 h / 75 °C 3: 45 percent / ozone, sodium bicarbonate / ethyl acetate / 8 h / 0 °C 4: 92 percent / NaBH4 / ethanol / 1.5 h / Ambient temperature 5: conc. HCl / CH2Cl2 / 31 h 6: AIBN, tri-n-butyltin hydride / toluene / 2 h / Heating 7: 93 percent / ozone / ethyl acetate / 0.5 h / -78 °C 8: SOCl2 / methanol / 2 h 9: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.08 h 10: 92 percent / PBr3 / petroleum ether / 1 h / 0 °C 11: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme

1: nBu4NCN / 8 h / 75 °C 2: 45 percent / ozone, sodium bicarbonate / ethyl acetate / 8 h / 0 °C 3: 92 percent / NaBH4 / ethanol / 1.5 h / Ambient temperature 4: conc. HCl / CH2Cl2 / 31 h 5: AIBN, tri-n-butyltin hydride / toluene / 2 h / Heating 6: 93 percent / ozone / ethyl acetate / 0.5 h / -78 °C 7: SOCl2 / methanol / 2 h 8: 99 percent / NaBH4, CeCl3*7H2O / methanol / 0.08 h 9: 92 percent / PBr3 / petroleum ether / 1 h / 0 °C 10: 1) NaI, 2) NaBH4 / 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h View Scheme

Zeolite β in pentane 2 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

sulfuric acid T=0°C; 6 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

sodium tetrahydroborate; sodium iodide 1) DMSO, r.t., 15 min, 2) MeOH, 1.5 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 88 percent / mCPBA / ethyl acetate / 20 °C 2: 93 percent / nBuLi; DIPA / tetrahydrofuran / 20 °C 3: 77 percent / p-TsOH / toluene / Heating View Scheme