potassium carbonate in dimethyl sulfoxide T=85 - 90°C;

potassium carbonate in dimethyl sulfoxide T=85 - 90°C; 4 h;

potassium carbonate in dimethyl sulfoxide T=75°C; 3 h;

1: 85 percent / K2CO3 / acetone / Heating 2: 80 percent / toluene / 180 - 190 °C 3: 1.) O3, 2.) NaBH3CN / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, i-PrOH 4: 72 percent / 135 °C 5: HN(SiMe3)2 / CH2Cl2; pentane / -20 °C 6: (PhSe)2 / tetrahydrofuran 7: 1.) O3, 2.) i-Pr2NH / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2 8: methanol / Heating 9: K2CO3, LiI / acetonitrile / 50 °C 10: 53 percent / PPh3, Et3N / Pd(OAc)2 / 90 °C 11: 67 percent / LiN(SiMe3)2 / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 12: Zn, H2SO4 / methanol / Heating 13: NaH / methanol / Heating 14: 65 percent / DIBAL / toluene / -40 °C 15: 49 percent / Ac2O, NaOAc / acetic acid / 110 °C View Scheme

iron; acetic acid 2.5 h; Reflux;

potassium carbonate in acetone 3 h; Heating;