1: 83 percent / LiAlH4 / not given 3: propan-2-ol; xylene / 0 °C / Irradiation 4: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C 6: Li-HMDS / tetrahydrofuran / Ambient temperature 7: 80 percent 9: mesitylenesulfonylchloride / pyridine 11: Li / various solvent(s) View Scheme

With  ozone in  pyridine; ethyl acetate T=-78°C;   

Multi-step reaction with 2 steps 1: CH2Cl2 / -78 °C2: 49 percent / O3, / ethyl acetate; pyridine / -78 °C  

With  lithium aluminium tetrahydride in  not given  

Multi-step reaction with 6 steps 1: 83 percent / LiAlH4 / not given3: propan-2-ol; xylene / 0 °C / Irradiation4: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C6: Li-HMDS / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 8 steps 1: 83 percent / LiAlH4 / not given3: propan-2-ol; xylene / 0 °C / Irradiation4: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C6: Li-HMDS / tetrahydrofuran / Ambient temperature7: 80 percent  

Multi-step reaction with 10 steps 1: 83 percent / LiAlH4 / not given3: propan-2-ol; xylene / 0 °C / Irradiation4: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C6: Li-HMDS / tetrahydrofuran / Ambient temperature7: 80 percent9: mesitylenesulfonylchloride / pyridine