1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: 51 percent / Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1: With triethylsilane; trifluoroacetic acid T=0 - 5°C; 0.5 h; 2: T=20°C; 20 h;

1: 63 percent / Et3SiH / trifluoroacetic acid 2: 69 percent / K2CO3, Bu4NBr / Pd(OAc)2 3: 1.) OsO4, (DHQD)2-Pyr, 2.) I2, CaCO3 4: 47 percent / ICl 5: 72 percent / aq. HI 6: 88 percent / NaH, LiBr / 1,2-dimethoxy-ethane; dimethylformamide 7: Me3SnSnMe3 / benzene / 70 °C / Irradiation View Scheme

1.1: 78 percent / NaBH4 / ethanol / 1 h / -40 °C 2.1: i-Pr2EtN / CH2Cl2 / 0 - 20 °C 3.1: i-PrMgCl / tetrahydrofuran / 1 h / -40 °C 3.2: CuCN*2LiCl / tetrahydrofuran / 0.25 h / -40 °C 3.3: 69 percent / tetrahydrofuran / 1.25 h / -40 - 20 °C 4.1: t-BuOK / tetrahydrofuran / 1 h / 0 °C 4.2: 27 percent / tetrahydrofuran / 36 h / Heating 5.1: 96 percent / LAH / diethyl ether 6.1: t-BuOOH; Ti(O-i-Pr)4; L-(+)-diethyl tartrate / 4 Angstroem molecular sieves / CH2Cl2; decane / 2 h / -20 °C 7.1: LAH / diethyl ether / 0 - 20 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 3 h / 20 °C 9.1: sodium chlorite; sodium dihydrogen phosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 16 h / 20 °C 10.1: TFA / 16 h / 20 °C 11.1: ICl / CCl4; CH2Cl2 / 24 h / 0 - 20 °C 12.1: chlorotrimethylsilane; H2O; NaI / acetonitrile / 5 h / 65 °C 13.1: sodium hydride; LiBr / 1,2-dimethoxy-ethane; dimethylformamide / 20 h / 70 °C 14.1: hexamethylditin / benzene / 1.5 h / Photolysis View Scheme