1: 91 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 3 h / -15 °C 2: 95 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C 3: 92 percent / NaHCO3; DDQ / CH2Cl2; H2O / 8 h / 0 °C 4: 84 percent / NaHCO3; mCPBA / CH2Cl2 / 3 h / -15 - 0 °C 5: 70 percent / dimethylformamide / 48 h / 70 °C 6: 91 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -40 °C 7: 91 percent / molecular sieves 4 Angstroem; NMO; TPAP / CH2Cl2 / 3 h / 20 °C 8: 68 percent / LHMDS / tetrahydrofuran; hexane / 3 h / -78 - 20 °C 9: 85 percent / HCl / methanol / 10 h / -20 °C 10: 98 percent / triethylamine; DMAP / CH2Cl2 / 1.5 h / 0 °C 11: 97 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12: 36 percent / Amberlyst 15 / tetrahydrofuran; H2O / 20 h / 20 °C View Scheme