potassium carbonate in acetone 3 h; Heating;

1: 72 percent / K2CO3 / dimethylsulfoxide / 85 - 90 °C 2: 85 percent / K2CO3 / acetone / Heating View Scheme

1: 72 percent / K2CO3 / dimethylsulfoxide / 85 - 90 °C 2: 85 percent / K2CO3 / acetone / Heating View Scheme

1: 72 percent / K2CO3 / dimethylsulfoxide / 4 h / 85 - 90 °C 2: 85 percent / K2CO3 / acetone / 3 h / Heating View Scheme

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