1: NaBH4 / ethanol 2: 96 percent / diethyl ether; tetrahydrofuran / Heating 3: pyridine / 0 °C 4: NaI / dimethylformamide; pyridine / 100 °C 5: hydrogen / Pd/C / ethanol / 25 °C 6: EtONa / ethanol / 25 °C 7: 95 percent / m-CPBA / CH2Cl2 / 25 °C 8: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 9: 95 percent / PCC / CH2Cl2 / 25 °C 10: EtONa / ethanol / 25 °C 11: tetrahydrofuran / 25 °C 12: 96 percent / pyridine / 25 °C 13: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 14: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 15: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 16: 89 percent / tetrahydrofuran / 25 °C 17: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 18: PCC / CH2Cl2 / 25 °C 19: 98 percent / tetrahydrofuran / 25 °C 20: tetrahydrofuran / 1 h / -78 °C 21: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme