1: 94 percent / DIBAL / toluene / 0.5 h / -78 °C 2: 1) N-chlorosuccinimide, Me2S, 2) NEt3 / 1) toluene, -25 deg C, 5.5 h, 2) 20 min. 3: 91 percent / tetrahydrofuran / 1 h / -40 deg C to r.t. 4: 1) N-chlorosuccinimide, Me2S, 2) NEt3 / 1) toluene, -25 deg C, 5.5 h 2) 20 min 5: HBr, H2O / diethyl ether / 0.5 h / 0 °C 6: NaHCO3, Na2CO3 / H2O / 2.5 h / Ambient temperature 7: 80 percent / pyridine / 20 h / 0 °C 8: pyridine / CH2Cl2 / 0.33 h / -15 °C 9: 1) Bu4NOAc, 2) DMAP, Py / 1) CH3CN, 40 deg C, 50 min, 2) 3 h, r.t. 10: 93 percent / NaBH4 / ethanol 11: 93 percent / K2CO3 / methanol / 1 h / 0 °C 12: 1) methyl triflate, 2) N-methylimidazole / 1) THF, 0 deg C, 40 min, 2) THF 13: 89 percent / H2, NaOAc / 10percent Pd/C / methanol 14: 95 percent / CF3COOH / H2O; dioxane View Scheme