1: LiAlH4 / tetrahydrofuran 2: Et3N / CH2Cl2 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 2.) CH2Cl2 4: KCN, 18-crown-6*MeCN / acetonitrile 5: 0.1 M aq. HCl / tetrahydrofuran 6: PhI(OAc)2, I2 / benzene / Irradiation 7: HCl / dioxane / 40 °C 8: (COCl)2, DMF / benzene 9: pyridine, DMAP / toluene 10: 1.) O2, 2.) (MeO)3P / 1.) toluene, 80 deg C, 2.) toluene 11: 71 percent / Et3N, DMAP / CH2Cl2 12: 1.) O3, MeOH, 2.) p-NO2-C6H4COCl, Et3N, DMAP / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 13: 67 percent / BF3*Et2O / toluene / -78 °C 14: 100 percent / H2 / Pd(OH)2 / methanol; ethyl acetate; H2O View Scheme