1: 93 percent / benzene / 5 - 20 °C 2: 95 percent / dimethylformamide / 1.5 h / 60 °C 3: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 4: 95 percent / PhSH, air / 0.33 h / 95 - 100 °C 5: LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 1 h, 2.) CH2Cl2, -60 deg C 30 min 7: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 to -20 deg C, 4 h 8: 90 percent / KOH / ethanol; H2O / Ambient temperature 9: (COCl)2 / benzene / 1 h / Heating 10: Et3N / diethyl ether / -5 - 20 °C View Scheme

1: 83 percent / I2; AgO2CCF3 / CHCl3 / -5 °C 2: 80 percent / PBr3; pyridine / diethyl ether / -20 °C 3: 98 percent / NaN3 / dimethylformamide 4: 89 percent / PPh3; water / tetrahydrofuran 5: 29 percent / air / Pd(PPh3)4 / dimethylformamide / 0.58 h / 100 °C View Scheme

dimethyl sulfoxide; 1-propanephosphonic acid cyclic anhydride in ethyl acetate T=0 - 25°C; 3 h; Inert atmosphere; chemoselective reaction;

diisobutylaluminium hydride 1.) toluene, reflux, 3 h, 2.) toluene, from 0 deg C to RT; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;