1.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 2.1: 72 percent / aq. AcOH / 4 h / Heating 3.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 4.1: Et3N / 10 h / 20 °C 5.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 7.1: LDA / tetrahydrofuran / 1 h / -50 °C 7.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 8.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 9.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 10.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme

1.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 2.1: 72 percent / aq. AcOH / 4 h / Heating 3.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 4.1: Et3N / 10 h / 20 °C 5.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 7.1: LDA / tetrahydrofuran / 1 h / -50 °C 7.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 8.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 9.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 10.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C 11.1: 90 percent / Ph3P; DIAD / tetrahydrofuran / 20 °C View Scheme

1.1: 76 percent / CuBr / tetrahydrofuran; diethyl ether / 5 h / 20 °C 2.1: 72 percent / aq. AcOH / 4 h / Heating 3.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C 4.1: Et3N / 10 h / 20 °C 5.1: 71 percent / DIPEA; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 94 percent / H2 / Pd(OH)2/C / ethyl acetate / 12 h 7.1: LDA / tetrahydrofuran / 1 h / -50 °C 7.2: 75 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -50 - 0 °C 8.1: LiOH; H2O / tetrahydrofuran; methanol / 12 h / 0 - 20 °C 9.1: 210 mg / PhSO2Cl; pyridine / 12 h / 0 °C 10.1: 88 percent / BF3*Et2O; ethane-1,2-dithiol / CH2Cl2 / 1 h / 0 °C View Scheme