1: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 2: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 3: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 99.6 percent / Et3N / dioxane / 14 h / 50 °C 2: 245 mg / 2M LiBH4 / tetrahydrofuran; diethyl ether / 15 h / Ambient temperature 3: 99 percent / DMAP, pyridine / 20 h / Ambient temperature 4: 134 mg / Ac2O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h 5: 94 percent / pyridine / 18 h / Ambient temperature 6: 90 mg / RuCl3, NaIO4 / ethyl acetate; acetonitrile; H2O / 5 h / Ambient temperature 7: 61 percent / 2-methyl-propan-2-ol; CH2Cl2 / 1 h / 50 °C 8: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 9: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 10: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 11: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 61 percent / 2-methyl-propan-2-ol; CH2Cl2 / 1 h / 50 °C 2: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 3: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 4: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 5: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 99 percent / DMAP, pyridine / 20 h / Ambient temperature 2: 134 mg / Ac2O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h 3: 94 percent / pyridine / 18 h / Ambient temperature 4: 90 mg / RuCl3, NaIO4 / ethyl acetate; acetonitrile; H2O / 5 h / Ambient temperature 5: 61 percent / 2-methyl-propan-2-ol; CH2Cl2 / 1 h / 50 °C 6: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 7: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 8: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 9: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 245 mg / 2M LiBH4 / tetrahydrofuran; diethyl ether / 15 h / Ambient temperature 2: 99 percent / DMAP, pyridine / 20 h / Ambient temperature 3: 134 mg / Ac2O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h 4: 94 percent / pyridine / 18 h / Ambient temperature 5: 90 mg / RuCl3, NaIO4 / ethyl acetate; acetonitrile; H2O / 5 h / Ambient temperature 6: 61 percent / 2-methyl-propan-2-ol; CH2Cl2 / 1 h / 50 °C 7: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 8: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 9: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 10: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 2: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 3: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 4: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 94 percent / pyridine / 18 h / Ambient temperature 2: 90 mg / RuCl3, NaIO4 / ethyl acetate; acetonitrile; H2O / 5 h / Ambient temperature 3: 61 percent / 2-methyl-propan-2-ol; CH2Cl2 / 1 h / 50 °C 4: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 5: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 6: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 7: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 90 mg / RuCl3, NaIO4 / ethyl acetate; acetonitrile; H2O / 5 h / Ambient temperature 2: 61 percent / 2-methyl-propan-2-ol; CH2Cl2 / 1 h / 50 °C 3: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 4: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 5: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 6: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

1: 134 mg / Ac2O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h 2: 94 percent / pyridine / 18 h / Ambient temperature 3: 90 mg / RuCl3, NaIO4 / ethyl acetate; acetonitrile; H2O / 5 h / Ambient temperature 4: 61 percent / 2-methyl-propan-2-ol; CH2Cl2 / 1 h / 50 °C 5: 95 percent / Zn / acetic acid; tetrahydrofuran / 3 h / Ambient temperature 6: 94 percent / (COCl)2, DMSO, Et3N / CH2Cl2 / -78 deg C then 0 deg C, 2 h 7: 88 percent / 1M NaBH3CN / methanol; tetrahydrofuran / 19 h / 0 - 7 °C 8: 89 percent / 1.) 20percent aq. HCl, anisole; 2.) 1N NaOH; 3.) Dowex 50Wx4 / 1.) THF, rt., 24 h; 2.) rt., 22 h; 3.) H2O then 15percent aq. NH3 View Scheme

hydrogenchloride; methoxybenzene in tetrahydrofuran; water 17 h; Ambient temperature;