1: pyridine / 18 h 2: 1.) sodium hydride, 2.) 1-<(2,4,6-triisopropylphenyl)sulfonyl>imidazole / 1.) HMPA, from 0 deg C to 25 deg C, 2 h, 2.) HMPA, THF, from -23 deg C to 0 deg C, 3 h 3: 95 percent / LiAlH4 / diethyl ether / -15 °C 4: 90 percent / Li, NH3 (liquid) / tetrahydrofuran 5: 87 percent / pyridine / 1 h / 25 °C 6: toluene / 7 h / Irradiation 7: imidazole / dimethylformamide / 23 °C 8: 1.) O3, 2.) dimethyl sulfide / 1.) methanol 9: CH2Cl2 / 18 h 11: 10percent aq. HCl / tetrahydrofuran / 0.33 h / 45 - 55 °C 12: Ag2CO3/Celite / toluene / 2 h / 95 °C View Scheme

1.1: 7.4 g / PTSA / toluene / 6 h / Heating 2.1: 78 percent / NaH; TBAI / tetrahydrofuran / 4 h / Heating 3.1: 79 percent / PTSA / methanol / 12 h 4.1: 83 percent / imidazole / CH2Cl2 / 4 h / 20 °C 5.1: NaH / 4 h 5.2: 78 percent / 12 h 6.1: 79 percent / AIBN; n-Bu3SnH / toluene / 1.5 h / Heating 7.1: 98 percent / TBAF / tetrahydrofuran / 2 h / 25 °C 8.1: 92 percent / Et3N / CH2Cl2 / 3 h / 20 °C 9.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 10.1: 72 percent / aq. AcOH / 4 h / Heating 11.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 12.1: Et3N / 10 h / 20 °C 13.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 14.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 15.1: LDA / tetrahydrofuran / 1 h / -50 °C 15.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 16.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 17.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 18.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme

1.1: 7.4 g / PTSA / toluene / 6 h / Heating 2.1: 78 percent / NaH; TBAI / tetrahydrofuran / 4 h / Heating 3.1: 79 percent / PTSA / methanol / 12 h 4.1: 83 percent / imidazole / CH2Cl2 / 4 h / 20 °C 5.1: NaH / 4 h 5.2: 78 percent / 12 h 6.1: 79 percent / AIBN; n-Bu3SnH / toluene / 1.5 h / Heating 7.1: 98 percent / TBAF / tetrahydrofuran / 2 h / 25 °C 8.1: 92 percent / Et3N / CH2Cl2 / 3 h / 20 °C 9.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 10.1: 72 percent / aq. AcOH / 4 h / Heating 11.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 12.1: Et3N / 10 h / 20 °C 13.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 14.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 15.1: LDA / tetrahydrofuran / 1 h / -50 °C 15.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 16.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 17.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 18.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / Ph3P; DIAD / tetrahydrofuran / 20 °C View Scheme

1.1: 7.4 g / PTSA / toluene / 6 h / Heating 2.1: 78 percent / NaH; TBAI / tetrahydrofuran / 4 h / Heating 3.1: 79 percent / PTSA / methanol / 12 h 4.1: 83 percent / imidazole / CH2Cl2 / 4 h / 20 °C 5.1: NaH / 4 h 5.2: 78 percent / 12 h 6.1: 79 percent / AIBN; n-Bu3SnH / toluene / 1.5 h / Heating 7.1: 98 percent / TBAF / tetrahydrofuran / 2 h / 25 °C 8.1: 92 percent / Et3N / CH2Cl2 / 3 h / 20 °C 9.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 10.1: 72 percent / aq. AcOH / 4 h / Heating 11.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 12.1: Et3N / 10 h / 20 °C 13.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 14.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 15.1: LDA / tetrahydrofuran / 1 h / -50 °C 15.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 16.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 17.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 18.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme