1: 1) ozone, 2) BH3*Me2S / 1) CH2Cl2, -78 deg C, 1 h, 2) CH2Cl2, THF, RT, 16 h 2: 86 percent / pyridine / 1 h / 0 °C 3: CH2Cl2 / 0 deg C, 15 min; RT, 2 h 4: hydrogen / Raney Ni / methanol / 2 h / sonication 5: Et3N / CH2Cl2 / 0.5 h 6: 74 percent / 4-(1-dimethylamino)pyridine / acetonitrile / 2.5 h / Ambient temperature 7: 91 percent / NaBH4, CaCl2 / ethanol; tetrahydrofuran / -20 deg C, 15 min; RT, 45 min 8: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -60 deg C, 15 min, 2) CH2Cl2, -60 deg C, 30 min 9: 1) potassium hexamethyldisilazide, 18-crown-6 / 1) THF, toluene, 1 h, -78 deg C, 2) THF, toluene, -78 deg C, 2 h 10: 71 percent / OsO4, Me3NO*2H2O / acetone; H2O / 2 h / Ambient temperature; sonication 11: 90 percent / NaOAc, hydrogen / Pd/C / methanol / Rt, 1 h; 35 deg C, 2 h 12: 97 percent / Dowex 50W400 / 4 h / Ambient temperature 13: 1) BH3*Me2S, 2) EtOH / 1) THF, 14 h, RT, 2) 2 h, reflux 14: 1) HCl, 2) Dowex 1X8-200 / 1) reflux, 30 min View Scheme