1: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 2: 47 percent / ICl 3: 72 percent / aq. HI 4: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 5: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 2: 47 percent / ICl 3: 72 percent / aq. HI 4: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 5: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 2: 47 percent / ICl 3: 72 percent / aq. HI 4: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 5: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 2: 47 percent / ICl 3: 72 percent / aq. HI 4: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 5: 51 percent / Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 2: 47 percent / ICl 3: 72 percent / aq. HI 4: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 5: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 2: 47 percent / ICl 3: 72 percent / aq. HI 4: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 5: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme