1: Et3N; DMAP / CH2Cl2 / 20 °C 2: NaN3 / dimethylformamide / 24 h / 80 °C 3: H2 / Pd/C / ethanol View Scheme

1: 96.5 percent / p-TsOH*H2O / toluene / 1 h / Heating 2: 93.5 percent / aq. NaOH / methanol / 13.5 h / Ambient temperature 3: 96.2 percent / (COCl)2, Et3N / CH2Cl2; dimethylsulfoxide / 2.5 h / -78 °C 4: 1.) AcOOH, AcOH, 2.) Me2S, 3.) conc. HCl 5: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature 6: 96.3 percent / p-TsOH*H2O / toluene / 1 h / Heating 7: 97.3 percent / NaBH4 / tetrahydrofuran; ethanol; H2O / 2 h / Ambient temperature 8: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 9: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 10: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 11: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 12: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 13: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 14: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature 2: 96.3 percent / p-TsOH*H2O / toluene / 1 h / Heating 3: 97.3 percent / NaBH4 / tetrahydrofuran; ethanol; H2O / 2 h / Ambient temperature 4: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 5: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 6: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 7: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 8: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 9: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 10: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 96.2 percent / (COCl)2, Et3N / CH2Cl2; dimethylsulfoxide / 2.5 h / -78 °C 2: 1.) AcOOH, AcOH, 2.) Me2S, 3.) conc. HCl 3: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature 4: 96.3 percent / p-TsOH*H2O / toluene / 1 h / Heating 5: 97.3 percent / NaBH4 / tetrahydrofuran; ethanol; H2O / 2 h / Ambient temperature 6: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 7: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 8: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 9: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 10: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 11: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 12: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 1.) AcOOH, AcOH, 2.) Me2S, 3.) conc. HCl 2: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature 3: 96.3 percent / p-TsOH*H2O / toluene / 1 h / Heating 4: 97.3 percent / NaBH4 / tetrahydrofuran; ethanol; H2O / 2 h / Ambient temperature 5: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 6: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 7: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 8: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 9: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 10: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 11: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 93.5 percent / aq. NaOH / methanol / 13.5 h / Ambient temperature 2: 96.2 percent / (COCl)2, Et3N / CH2Cl2; dimethylsulfoxide / 2.5 h / -78 °C 3: 1.) AcOOH, AcOH, 2.) Me2S, 3.) conc. HCl 4: 93.8 percent / imidazole / dimethylformamide / 3 h / Ambient temperature 5: 96.3 percent / p-TsOH*H2O / toluene / 1 h / Heating 6: 97.3 percent / NaBH4 / tetrahydrofuran; ethanol; H2O / 2 h / Ambient temperature 7: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 8: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 9: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 10: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 11: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 12: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 13: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 96.3 percent / p-TsOH*H2O / toluene / 1 h / Heating 2: 97.3 percent / NaBH4 / tetrahydrofuran; ethanol; H2O / 2 h / Ambient temperature 3: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 4: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 5: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 6: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 7: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 8: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 9: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 2: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 3: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 4: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 5: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 6: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 7: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 97.3 percent / NaBH4 / tetrahydrofuran; ethanol; H2O / 2 h / Ambient temperature 2: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 38.5 h / Ambient temperature 3: 89.3 percent / Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 4: 74.5 percent / Pr4NRuO4, N-methylmorpholine-N-oxide, MS 4Angstroem / CH2Cl2 / 1 h / Ambient temperature 5: 1.) n-BuLi / 1.) hexane, 0 deg C, 3 h, 2.) hexane, THF, RT, 5 h 6: 99.5 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature 7: 81.7 percent / 90percent aq. AcOH / 22.5 h / Ambient temperature 8: 62.6 percent / 1,5-dimethoxynaphthalene, NaBH4 / ethanol; H2O / 10 h / Ambient temperature; Irradiation View Scheme

1: 97 percent / CuI 2: 93 percent / i-Pr2NEt 3: H2 / Pd-C 4: 98 percent / pyridine 5: 83 percent / NaN3 6: AcOH, H2O 7: Ph3P / H2O; pyridine View Scheme