Amberlyst 15; sodium iodide in acetone T=20°C; deoxygenation; 6 h;

acetic acid; sodium phenylseleno(triethyl)borate in ethanol T=20°C; Reduction; dehydration; 0.166667 h;

W-2 Raney nickel in acetone T=20°C; 4 h;

boron trifluoride diethyl etherate; ethanethiol in dichloromethane T=30°C; 18 h;

copper dichloride in methanol; water 20 h; Heating;

toluene-4-sulfonic acid in ethanol 1 h; Ambient temperature;

2: Li, liquid ammonia, t-butanol 3: 97 percent / potassium t-butoxide / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 4: 2) silica gel / 1) Et2O, hexane, r.t., 30 min, 2) r.t., 15 h 5: diethyl ether; hexane / 0.67 h / 0 °C 6: 63 percent / POCl3, pyridine / 12 h / Ambient temperature 7: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature 8: 51.8 mg / SO3*pyridine, NEt3 / dimethylsulfoxide / 0.33 h / Ambient temperature 9: 29.8 mg / NH2OH*HCl, NaOAc / methanol / 2 h / Ambient temperature 10: 87 percent / 6percent aq.NaOCl / CH2Cl2 / Ambient temperature 11: 97 percent / B(OMe)3, H2 / Raney-Ni (W-2) / methanol; H2O / 20 h / 750.06 Torr / Ambient temperature 12: 97 percent / SO3*pyridine, NEt3 / dimethylsulfoxide / 1.5 h / Ambient temperature 13: 89 percent / xylene / 90 h / Heating 14: H2 / 10percent Pd/C / ethanol / 6 h / 2250.2 Torr / Ambient temperature 15: 43.8 mg / 10percent aq.KOH / methanol / 4 h / Ambient temperature 16: 86 percent / CF3CO2H / 1.17 h / Ambient temperature View Scheme

1: Li, liquid ammonia, t-butanol 2: 97 percent / potassium t-butoxide / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 3: 2) silica gel / 1) Et2O, hexane, r.t., 30 min, 2) r.t., 15 h 4: diethyl ether; hexane / 0.67 h / 0 °C 5: 63 percent / POCl3, pyridine / 12 h / Ambient temperature 6: 99 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature 7: 51.8 mg / SO3*pyridine, NEt3 / dimethylsulfoxide / 0.33 h / Ambient temperature 8: 29.8 mg / NH2OH*HCl, NaOAc / methanol / 2 h / Ambient temperature 9: 87 percent / 6percent aq.NaOCl / CH2Cl2 / Ambient temperature 10: 97 percent / B(OMe)3, H2 / Raney-Ni (W-2) / methanol; H2O / 20 h / 750.06 Torr / Ambient temperature 11: 97 percent / SO3*pyridine, NEt3 / dimethylsulfoxide / 1.5 h / Ambient temperature 12: 89 percent / xylene / 90 h / Heating 13: H2 / 10percent Pd/C / ethanol / 6 h / 2250.2 Torr / Ambient temperature 14: 43.8 mg / 10percent aq.KOH / methanol / 4 h / Ambient temperature 15: 86 percent / CF3CO2H / 1.17 h / Ambient temperature View Scheme

aluminium trichloride; sodium iodide in acetonitrile 5 h; Ambient temperature;

trifluoroacetic acid