in water; ethyl acetate T=50 - 55°C; Michael addition; 24 h;

1: 80 percent / NaH / tetrahydrofuran / 72 h / 20 °C 2: 98 percent / H2 / Pd/C / ethyl acetate / 760 Torr 3: 75 percent / DIBAL-H / CH2Cl2; hexane / 30 h / -78 °C 4: 72 percent / KF / propan-2-ol / 20 °C 5: 92 percent / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.33 h / 0 °C 6: 78 percent / H2O; ethyl acetate / 24 h / 50 - 55 °C View Scheme

1: 98 percent / H2 / Pd/C / ethyl acetate / 760 Torr 2: 75 percent / DIBAL-H / CH2Cl2; hexane / 30 h / -78 °C 3: 72 percent / KF / propan-2-ol / 20 °C 4: 92 percent / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.33 h / 0 °C 5: 78 percent / H2O; ethyl acetate / 24 h / 50 - 55 °C View Scheme

1: 72 percent / KF / propan-2-ol / 20 °C 2: 92 percent / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.33 h / 0 °C 3: 78 percent / H2O; ethyl acetate / 24 h / 50 - 55 °C View Scheme

1: 75 percent / DIBAL-H / CH2Cl2; hexane / 30 h / -78 °C 2: 72 percent / KF / propan-2-ol / 20 °C 3: 92 percent / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.33 h / 0 °C 4: 78 percent / H2O; ethyl acetate / 24 h / 50 - 55 °C View Scheme

1: 92 percent / methanesulfonyl chloride; triethylamine / CH2Cl2 / 0.33 h / 0 °C 2: 78 percent / H2O; ethyl acetate / 24 h / 50 - 55 °C View Scheme