1: 1.) pig liver esterase, 2.) O3 / 1.) acetone, 30-32 deg C, 5 h, 2.) ethyl acetate, -78 deg C, 3 h 2: NaBH4 / methanol / 3 h / Heating 3: NaIO4 / 0.5 h / Ambient temperature 4: 2.42 g 5: 73 percent / p-(dimethylamino)pyridine, triethylamine / tetrahydrofuran / 16 h / Ambient temperature 6: 44.7 percent / silver trifluoroacetate / CH2Cl2 / 2 h / Ambient temperature 7: 87 percent / diisopropylethylamine / CH2Cl2 / 16 h / Ambient temperature 8: 108 mg / 0.13M NaOH / acetone / 2 h 9: 1.) triethylamine, ethyl chloroformate, 2.) sodium azide 10: 98.6 percent / O3 / CH2Cl2 / 0.25 h / -78 °C 11: 101 mg / 2.5N NaOH / methanol / 12 h / Heating 12: 116 mg / triethylamine / butan-1-ol / 40 h / Heating 13: 1.) acetic anhydride, 2.) NH3(gas) / 1.) room temperature, 2 h, 2.) methanol, 45 deg C, 16 h 14: 80 percent / 2M HCl / methanol / 16 h / Ambient temperature View Scheme