1: 77 percent / LiAlH4 / tetrahydrofuran / 3 h 2: 84 percent / pyridine / 4 °C 3: 77 percent / HgO, BF3*Et2O / 0.5 h 4: 94 percent / 0.2 M NaOMe / methanol / 16 h / 4 °C 5: 83 percent / 0.01 M trifluoroacetic acid / 24 h / 4 °C View Scheme

1: 87 percent / LiAlH4 / tetrahydrofuran / 3 h 2: 86 percent / pyridine / 4 °C 3: 65 percent / HgO, BF3*Et2O / 0.5 h 4: 95 percent / NaOMe / methanol / 16 h / 4 °C 5: 73 percent / 0.01 M trifluoroacetic acid / 24 h / 4 °C View Scheme