1: hydrogen / Pd/BaSO4 / ethanol 2: NaBH4 / ethanol 3: 96 percent / diethyl ether; tetrahydrofuran / Heating 4: pyridine / 0 °C 5: NaI / dimethylformamide; pyridine / 100 °C 6: hydrogen / Pd/C / ethanol / 25 °C 7: EtONa / ethanol / 25 °C 8: 95 percent / m-CPBA / CH2Cl2 / 25 °C 9: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 10: 95 percent / PCC / CH2Cl2 / 25 °C 11: EtONa / ethanol / 25 °C 12: tetrahydrofuran / 25 °C 13: 96 percent / pyridine / 25 °C 14: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 15: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 16: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 17: 89 percent / tetrahydrofuran / 25 °C 18: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 19: PCC / CH2Cl2 / 25 °C 20: 98 percent / tetrahydrofuran / 25 °C 21: tetrahydrofuran / 1 h / -78 °C 22: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme

2: 82 percent / H2 / 10percent Rh/C / ethyl acetate / 735.5 Torr 3: 57 percent / trifluoroperacetic acid, disodium hydrogen phosphate / CH2Cl2 / 1.) 0 deg C, 1 h; 2.) RT, 30 h 4: 80 percent / iodotrimethylsilane / CCl4 / 5 h / Ambient temperature 5: 97 percent / pyridinium chlorochromate; / CH2Cl2 / 2.5 h / Ambient temperature 6: 87 percent / 25percent NaOMe / methanol / 3.5 h 7: t-BuOK / tetrahydrofuran / 63 h / Ambient temperature 8: 70 percent / 0.813M BF3*Et2O / CH2Cl2 / 2 h 9: 77 percent / H2 / 5 percent Pd/C / ethyl acetate / 735.5 Torr View Scheme