potassium carbonate T=20°C; 16 h;

sodium hydroxide in dichloromethane; water T=25°C; Wittig reaction; Sonication; stereoselective reaction;

water; potassium carbonate

in dichloromethane T=20°C;

1: glutaric acid dimethyl ester With diisobutylaluminium hydride in diethyl ether; toluene T=-78°C; 0.5 h; 2: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride in tetrahydrofuran; diethyl ether; toluene T=-78 - 20°C; double Horner-Emmons addition; 2 h;

1H-imidazole in dichloromethane T=20°C; Wittig olefination; 19 h;

1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=20°C; 19 h;

1: silica supported pyridinium chlorochromate / CH2Cl2 / 4 h / 20 °C 2: 87 mg / imidazole / CH2Cl2 / 19 h / 20 °C View Scheme

potassium carbonate

1.1: 92 percent / DIBAH / tetrahydrofuran; toluene / 4 h / -78 °C 2.1: NaH / tetrahydrofuran / 1 h 2.2: 39 percent / tetrahydrofuran / 48 h / 70 °C 3.1: 73 percent / LiCl; n-BuLi; CH3SO2Cl / tetrahydrofuran; hexane / -78 - 20 °C 4.1: (-)-sparteine; n-BuLi / toluene; hexane / 2 h / -90 °C 5.1: n-BuLi; TMEDA / tetrahydrofuran; hexane / 4 h / -78 - 20 °C 5.2: tetrahydrofuran / 12 h / 40 °C View Scheme