hydrogenchloride in hexane; water; ethyl acetate; acetone

in methyl acetate; water

in sodium hydroxide; water; ethyl acetate; acetonitrile

1: 83 percent / i-Pr2NEt, N,N-(dimethylamino)pyridine / CH2Cl2 / 3 h / Ambient temperature 2: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 4: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 6: 91 percent / DBU / CH2Cl2 / 8 h 7: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 8: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

1: 1) O3, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 3: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 4: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 5: 91 percent / DBU / CH2Cl2 / 8 h 6: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 7: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

1: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 2: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 3: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 4: 91 percent / DBU / CH2Cl2 / 8 h 5: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 6: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

1: 72 percent / Et3N, acetyl chloride / 20 h / 0 °C 2: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 3: 91 percent / DBU / CH2Cl2 / 8 h 4: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 5: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

1: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C, 2 min 2: 91 percent / DBU / CH2Cl2 / 8 h 3: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 4: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

1: 91 percent / DBU / CH2Cl2 / 8 h 2: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 3: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme

1: 93 percent / oxone, NaHCO3 / H2O; methanol / 18 h / Ambient temperature; pH 3 2: 96 percent / H2 / Pd/C / ethyl acetate / 1 h / Ambient temperature View Scheme