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

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

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

1: hydrogen / Pd/C / ethanol / 25 °C 2: EtONa / ethanol / 25 °C 3: 95 percent / m-CPBA / CH2Cl2 / 25 °C 4: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 5: 95 percent / PCC / CH2Cl2 / 25 °C 6: EtONa / ethanol / 25 °C 7: tetrahydrofuran / 25 °C 8: 96 percent / pyridine / 25 °C 9: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 10: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 11: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 12: 89 percent / tetrahydrofuran / 25 °C 13: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 14: PCC / CH2Cl2 / 25 °C 15: 98 percent / tetrahydrofuran / 25 °C 16: tetrahydrofuran / 1 h / -78 °C 17: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme

1: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 2: 95 percent / PCC / CH2Cl2 / 25 °C 3: EtONa / ethanol / 25 °C 4: tetrahydrofuran / 25 °C 5: 96 percent / pyridine / 25 °C 6: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 7: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 8: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 9: 89 percent / tetrahydrofuran / 25 °C 10: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 11: PCC / CH2Cl2 / 25 °C 12: 98 percent / tetrahydrofuran / 25 °C 13: tetrahydrofuran / 1 h / -78 °C 14: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme

1: 96 percent / diethyl ether; tetrahydrofuran / Heating 2: pyridine / 0 °C 3: NaI / dimethylformamide; pyridine / 100 °C 4: hydrogen / Pd/C / ethanol / 25 °C 5: EtONa / ethanol / 25 °C 6: 95 percent / m-CPBA / CH2Cl2 / 25 °C 7: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 8: 95 percent / PCC / CH2Cl2 / 25 °C 9: EtONa / ethanol / 25 °C 10: tetrahydrofuran / 25 °C 11: 96 percent / pyridine / 25 °C 12: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 13: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 14: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 15: 89 percent / tetrahydrofuran / 25 °C 16: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 17: PCC / CH2Cl2 / 25 °C 18: 98 percent / tetrahydrofuran / 25 °C 19: tetrahydrofuran / 1 h / -78 °C 20: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme

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

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

1: pyridine / 0 °C 2: NaI / dimethylformamide; pyridine / 100 °C 3: hydrogen / Pd/C / ethanol / 25 °C 4: EtONa / ethanol / 25 °C 5: 95 percent / m-CPBA / CH2Cl2 / 25 °C 6: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 7: 95 percent / PCC / CH2Cl2 / 25 °C 8: EtONa / ethanol / 25 °C 9: tetrahydrofuran / 25 °C 10: 96 percent / pyridine / 25 °C 11: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 12: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 13: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 14: 89 percent / tetrahydrofuran / 25 °C 15: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 16: PCC / CH2Cl2 / 25 °C 17: 98 percent / tetrahydrofuran / 25 °C 18: tetrahydrofuran / 1 h / -78 °C 19: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme