2: propan-2-ol; xylene / 0 °C / Irradiation 3: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C 5: Li-HMDS / tetrahydrofuran / Ambient temperature 6: 80 percent 8: mesitylenesulfonylchloride / pyridine 10: Li / various solvent(s) View Scheme

With  lithium aluminium tetrahydride in  not given  

Multi-step reaction with 3 steps 1: CH2Cl2 / -78 °C2: 49 percent / O3, / ethyl acetate; pyridine / -78 °C3: 83 percent / LiAlH4 / not given  

Multi-step reaction with 2 steps 1: 49 percent / O3, / ethyl acetate; pyridine / -78 °C2: 83 percent / LiAlH4 / not given  

Multi-step reaction with 5 steps 2: propan-2-ol; xylene / 0 °C / Irradiation3: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C5: Li-HMDS / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 7 steps 2: propan-2-ol; xylene / 0 °C / Irradiation3: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C5: Li-HMDS / tetrahydrofuran / Ambient temperature6: 80 percent  

Multi-step reaction with 9 steps 2: propan-2-ol; xylene / 0 °C / Irradiation3: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C5: Li-HMDS / tetrahydrofuran / Ambient temperature6: 80 percent8: mesitylenesulfonylchloride / pyridine