sodium periodate; osmium(VIII) oxide in diethyl ether; water oxidative cleavage;

1.1: 90 percent / OsO4, NaIO4 / diethyl ether; H2O 2.1: diethyl ether / 4 h / -78 °C 2.2: 91 percent / water / 12 h 3.1: 98 percent / t-BuOK / tetrahydrofuran 4.1: O3 / CH2Cl2; methanol / -78 °C 4.2: 83 percent / NaBH4, aq. NaOH View Scheme

1.1: 90 percent / OsO4, NaIO4 / diethyl ether; H2O 2.1: diethyl ether / 4 h / -78 °C 2.2: 91 percent / water / 12 h View Scheme