1: 75 percent / 1.) sudan red, ozone; 2.) Me2S / CH2Cl2; methanol / 1.) -70 deg C, 5 h; 2.) to rt 2: 90 percent / O3 / CH2Cl2; methanol 3: LiAlH4 / tetrahydrofuran / Ambient temperature 4: 98 percent / 1.) NaH; 2.) tetrabutylammonium iodide / tetrahydrofuran / 2 h / Ambient temperature 5: 87 percent Spectr. / POCl3 / pyridine; CH2Cl2 / 48 h / -30 °C 6: 93 percent / sodium / diethyl ether; liquid ammonia / 0.67 h / -40 °C 7: 90 percent / pyridinium chlorochromate / CH2Cl2 / 1.25 h / Ambient temperature View Scheme

1: 75 percent / 1.) sudan red, ozone; 2.) Me2S / CH2Cl2; methanol / 1.) -70 deg C, 5 h; 2.) to rt 2: 90 percent / O3 / CH2Cl2; methanol 3: LiAlH4 / tetrahydrofuran / Ambient temperature 4: 92 percent / ZnCl2 / 1,2-dichloro-ethane / 3 h View Scheme