1: 95 percent / PCC / CH2Cl2 / 25 °C 2: EtONa / ethanol / 25 °C 3: tetrahydrofuran / 25 °C 4: 96 percent / pyridine / 25 °C 5: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 6: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 7: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 8: 89 percent / tetrahydrofuran / 25 °C 9: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 10: PCC / CH2Cl2 / 25 °C 11: 98 percent / tetrahydrofuran / 25 °C 12: tetrahydrofuran / 1 h / -78 °C 13: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme

1: 97 percent / pyridinium chlorochromate; / CH2Cl2 / 2.5 h / Ambient temperature 2: 87 percent / 25percent NaOMe / methanol / 3.5 h 3: t-BuOK / tetrahydrofuran / 63 h / Ambient temperature 4: 70 percent / 0.813M BF3*Et2O / CH2Cl2 / 2 h 5: 77 percent / H2 / 5 percent Pd/C / ethyl acetate / 735.5 Torr View Scheme