1: With Zhan 1b catalyst in dichloromethane Olefin cross-metathesis; 48 h; Inert atmosphereReflux; 2: With water; Dess-Martin periodane in dichloromethane T=0°C; Dess-Martin oxidation; 3: With ammonium acetate; acetic acid in ethanol T=55°C; 24 h;

1: 70 percent / Et3N / diethyl ether / Ambient temperature 2: 1) (COCl)2, DMSO, 3) Et3N 3: 55 percent / H2, 42percent aq. HBF3 / Raney Ni / ethanol / 16 h / 760 Torr / Ambient temperature View Scheme

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h 2: Zhan 1b catalyst / dichloromethane / 48 h / Inert atmosphere; Reflux 3: ammonium acetate; water / ethanol / 48 h / 90 °C View Scheme

sodium hydrogencarbonate; Dess-Martin periodane in dichloromethane Dess-Martin oxidation; 1 h;