1: CH2Cl2 / -78 °C 2: 49 percent / O3, / ethyl acetate; pyridine / -78 °C 3: 83 percent / LiAlH4 / not given 5: propan-2-ol; xylene / 0 °C / Irradiation 6: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C 8: Li-HMDS / tetrahydrofuran / Ambient temperature 9: 80 percent 11: mesitylenesulfonylchloride / pyridine 13: Li / various solvent(s) View Scheme

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

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 8 steps 1: CH2Cl2 / -78 °C2: 49 percent / O3, / ethyl acetate; pyridine / -78 °C3: 83 percent / LiAlH4 / not given5: propan-2-ol; xylene / 0 °C / Irradiation6: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C8: Li-HMDS / tetrahydrofuran / Ambient temperature  

Multi-step reaction with 10 steps 1: CH2Cl2 / -78 °C2: 49 percent / O3, / ethyl acetate; pyridine / -78 °C3: 83 percent / LiAlH4 / not given5: propan-2-ol; xylene / 0 °C / Irradiation6: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C8: Li-HMDS / tetrahydrofuran / Ambient temperature9: 80 percent  

Multi-step reaction with 12 steps 1: CH2Cl2 / -78 °C2: 49 percent / O3, / ethyl acetate; pyridine / -78 °C3: 83 percent / LiAlH4 / not given5: propan-2-ol; xylene / 0 °C / Irradiation6: 71 percent / OsO4, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C8: Li-HMDS / tetrahydrofuran / Ambient temperature9: 80 percent11: mesitylenesulfonylchloride / pyridine