1.1: thiocarbonyl diimidazole; 4-DMAP / tetrahydrofuran / 95 °C 1.2: n-Bu3SnH; AIBN / benzene / 1 h / 80 °C 2.1: (CF3CO2)2IC6H5 / methanol; tetrahydrofuran / 20 °C 2.2: 95 percent / p-TsOH / dioxane; H2O / 50 °C 3.1: LDA / tetrahydrofuran / -78 °C 4.1: RuBnCl2(PCy3)2 / benzene / 24 h / 20 °C 5.1: Dess-Martin periodinane / CH2Cl2 / 20 °C 6.1: NaBH4 / methanol; tetrahydrofuran / -78 - 20 °C 7.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 8.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 9.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 10.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 11.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1.1: thiocarbonyl diimidazole; 4-DMAP / tetrahydrofuran / 95 °C 1.2: n-Bu3SnH; AIBN / benzene / 1 h / 80 °C 2.1: (CF3CO2)2IC6H5 / methanol; tetrahydrofuran / 20 °C 2.2: 95 percent / p-TsOH / dioxane; H2O / 50 °C 3.1: LDA / tetrahydrofuran / -78 °C 4.1: RuBnCl2(PCy3)2 / benzene / 24 h / 20 °C 5.1: Dess-Martin periodinane / CH2Cl2 / 20 °C 6.1: NaBH4 / methanol; tetrahydrofuran / -78 - 20 °C 7.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 8.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 9.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 10.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C View Scheme