1: 1.) ozone, 2.) dimethyl sulfide / 1a.) CH2Cl2, -78 deg C, 1 h, 1b.) RT, 0.5 h, 2.) RT, 1 h 2: 1.) sodium hydride / 1.) THF, 15 min, 2.) RT, 4 h 3: 98 percent / H2 / 10percent Pd/C / ethyl acetate / 0.5 h / 2068.6 Torr / Ambient temperature 4: 90 percent / DIBAH / toluene / 0.5 h / -78 °C 7: 79 percent / N,N-diisopropylethylamine / CH2Cl2 / 19 h / Ambient temperature 8: 1.) ozone, 2.) Me2S / 1a.) CH2Cl2, -78 deg C, 0.5 h, 1b.) RT, O.5 h, 2.) RT, 1 h 9: pyridinium dichromate / dimethylformamide / 17 h / Ambient temperature 10: dimethylformamide; H2O; diethyl ether / 1 h / Ambient temperature 11: 72 percent / ZnBr2 / CH2Cl2 / 3 h / Ambient temperature 12: 96 percent / aq. NaOH / propan-2-ol / 0.5 h / 60 °C 13: 48 percent / benzenesulfonyl chloride, pyridine 14: 44 percent / Zn, dibromoethane / tetrahydrofuran / 1.12 h / Heating 15: 30 percent / SOCl2, pyridine / CH2Cl2 / 0.08 h / Heating 16: 76 percent / 50percent aq. HF / tetrahydrofuran / 18 h / Ambient temperature View Scheme

With  dimethylsulfide; ozone  1a.) CH2Cl2, -78 deg C, 1 h, 1b.) RT, 0.5 h, 2.) RT, 1 h;  Multistep reaction;   

Multi-step reaction with 4 steps 1: 1.) ozone, 2.) dimethyl sulfide / 1a.) CH2Cl2, -78 deg C, 1 h, 1b.) RT, 0.5 h, 2.) RT, 1 h2: 1.) sodium hydride / 1.) THF, 15 min, 2.) RT, 4 h3: 98 percent / H2 / 10percent Pd/C / ethyl acetate / 0.5 h / 2068.6 Torr / Ambient temperature4: 90 percent / DIBAH / toluene / 0.5 h / -78 °C  

Multi-step reaction with 6 steps 1: 1.) ozone, 2.) dimethyl sulfide / 1a.) CH2Cl2, -78 deg C, 1 h, 1b.) RT, 0.5 h, 2.) RT, 1 h2: 1.) sodium hydride / 1.) THF, 15 min, 2.) RT, 4 h3: 98 percent / H2 / 10percent Pd/C / ethyl acetate / 0.5 h / 2068.6 Torr / Ambient temperature4: 90 percent / DIBAH / toluene / 0.5 h / -78 °C