1: 1) MeZnBr, 2) LDA / 1) THF, Et2O, 1 h, 0 deg C, 2) THF, Et2O, -78 deg C, 1 h, 3) THF, Et2O, -78 deg C 2: 77 percent / 2,6-lutidine / CH2Cl2 / 2 h / -78 °C 3: 1) ozone, 2) BH3*Me2S / 1) CH2Cl2, -78 deg C, 1 h, 2) CH2Cl2, THF, RT, 16 h 4: 86 percent / pyridine / 1 h / 0 °C 5: CH2Cl2 / 0 deg C, 15 min; RT, 2 h 6: hydrogen / Raney Ni / methanol / 2 h / sonication 7: Et3N / CH2Cl2 / 0.5 h 8: 74 percent / 4-(1-dimethylamino)pyridine / acetonitrile / 2.5 h / Ambient temperature 9: 91 percent / NaBH4, CaCl2 / ethanol; tetrahydrofuran / -20 deg C, 15 min; RT, 45 min 10: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -60 deg C, 15 min, 2) CH2Cl2, -60 deg C, 30 min 11: 1) potassium hexamethyldisilazide, 18-crown-6 / 1) THF, toluene, 1 h, -78 deg C, 2) THF, toluene, -78 deg C, 2 h 12: 71 percent / OsO4, Me3NO*2H2O / acetone; H2O / 2 h / Ambient temperature; sonication 13: 90 percent / NaOAc, hydrogen / Pd/C / methanol / Rt, 1 h; 35 deg C, 2 h 14: 97 percent / Dowex 50W400 / 4 h / Ambient temperature 15: 1) BH3*Me2S, 2) EtOH / 1) THF, 14 h, RT, 2) 2 h, reflux 16: 1) HCl, 2) Dowex 1X8-200 / 1) reflux, 30 min View Scheme

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

1: 77 percent / 2,6-lutidine / CH2Cl2 / 2 h / -78 °C 2: 1) ozone, 2) BH3*Me2S / 1) CH2Cl2, -78 deg C, 1 h, 2) CH2Cl2, THF, RT, 16 h 3: 86 percent / pyridine / 1 h / 0 °C 4: CH2Cl2 / 0 deg C, 15 min; RT, 2 h 5: hydrogen / Raney Ni / methanol / 2 h / sonication 6: Et3N / CH2Cl2 / 0.5 h 7: 74 percent / 4-(1-dimethylamino)pyridine / acetonitrile / 2.5 h / Ambient temperature 8: 91 percent / NaBH4, CaCl2 / ethanol; tetrahydrofuran / -20 deg C, 15 min; RT, 45 min 9: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -60 deg C, 15 min, 2) CH2Cl2, -60 deg C, 30 min 10: 1) potassium hexamethyldisilazide, 18-crown-6 / 1) THF, toluene, 1 h, -78 deg C, 2) THF, toluene, -78 deg C, 2 h 11: 71 percent / OsO4, Me3NO*2H2O / acetone; H2O / 2 h / Ambient temperature; sonication 12: 90 percent / NaOAc, hydrogen / Pd/C / methanol / Rt, 1 h; 35 deg C, 2 h 13: 97 percent / Dowex 50W400 / 4 h / Ambient temperature 14: 1) BH3*Me2S, 2) EtOH / 1) THF, 14 h, RT, 2) 2 h, reflux 15: 1) HCl, 2) Dowex 1X8-200 / 1) reflux, 30 min View Scheme

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

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

1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -60 deg C, 15 min, 2) CH2Cl2, -60 deg C, 30 min 2: 1) potassium hexamethyldisilazide, 18-crown-6 / 1) THF, toluene, 1 h, -78 deg C, 2) THF, toluene, -78 deg C, 2 h 3: 71 percent / OsO4, Me3NO*2H2O / acetone; H2O / 2 h / Ambient temperature; sonication 4: 90 percent / NaOAc, hydrogen / Pd/C / methanol / Rt, 1 h; 35 deg C, 2 h 5: 97 percent / Dowex 50W400 / 4 h / Ambient temperature 6: 1) BH3*Me2S, 2) EtOH / 1) THF, 14 h, RT, 2) 2 h, reflux 7: 1) HCl, 2) Dowex 1X8-200 / 1) reflux, 30 min View Scheme

1: 1) potassium hexamethyldisilazide, 18-crown-6 / 1) THF, toluene, 1 h, -78 deg C, 2) THF, toluene, -78 deg C, 2 h 2: 71 percent / OsO4, Me3NO*2H2O / acetone; H2O / 2 h / Ambient temperature; sonication 3: 90 percent / NaOAc, hydrogen / Pd/C / methanol / Rt, 1 h; 35 deg C, 2 h 4: 97 percent / Dowex 50W400 / 4 h / Ambient temperature 5: 1) BH3*Me2S, 2) EtOH / 1) THF, 14 h, RT, 2) 2 h, reflux 6: 1) HCl, 2) Dowex 1X8-200 / 1) reflux, 30 min View Scheme

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

1: 71 percent / OsO4, Me3NO*2H2O / acetone; H2O / 2 h / Ambient temperature; sonication 2: 90 percent / NaOAc, hydrogen / Pd/C / methanol / Rt, 1 h; 35 deg C, 2 h 3: 97 percent / Dowex 50W400 / 4 h / Ambient temperature 4: 1) BH3*Me2S, 2) EtOH / 1) THF, 14 h, RT, 2) 2 h, reflux 5: 1) HCl, 2) Dowex 1X8-200 / 1) reflux, 30 min View Scheme

1: 90 percent / NaOAc, hydrogen / Pd/C / methanol / Rt, 1 h; 35 deg C, 2 h 2: 97 percent / Dowex 50W400 / 4 h / Ambient temperature 3: 1) BH3*Me2S, 2) EtOH / 1) THF, 14 h, RT, 2) 2 h, reflux 4: 1) HCl, 2) Dowex 1X8-200 / 1) reflux, 30 min View Scheme