1.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 1.2: Et3N / CH2Cl2 / -78 - 20 °C 2.1: diethyl ether / 0 - 20 °C 3.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH2Cl2 / 0 - 20 °C 4.1: n-BuLi / tetrahydrofuran / -78 °C 4.2: 97 percent / tetrahydrofuran / -78 - 20 °C 5.1: 64 percent / N-iodosuccinimide; AgNO3 / acetone 6.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether 7.1: 86 percent / PhSH; BF3*OEt2 / CH2Cl2 / 20 °C 8.1: 99 percent / pyridine; 4-DMAP / CH2Cl2 / 20 °C 9.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 9.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 10.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 11.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 12.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 13.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 14.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 15.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C 16.1: 49 percent / 3,3-dimethyldioxirane / CH2Cl2; acetone / 2 h / -50 - -30 °C View Scheme

1.1: (COCl)2; DMSO / CH2Cl2 / -78 °C 1.2: Et3N / CH2Cl2 / -78 - 20 °C 2.1: diethyl ether / 0 - 20 °C 3.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH2Cl2 / 0 - 20 °C 4.1: n-BuLi / tetrahydrofuran / -78 °C 4.2: 97 percent / tetrahydrofuran / -78 - 20 °C 5.1: 64 percent / N-iodosuccinimide; AgNO3 / acetone 6.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether 7.1: 86 percent / PhSH; BF3*OEt2 / CH2Cl2 / 20 °C 8.1: 99 percent / pyridine; 4-DMAP / CH2Cl2 / 20 °C 9.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C 9.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C 10.1: 85 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 11.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C 12.1: 99 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 13.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 14.1: 84 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 15.1: 99 percent / HF*pyridine / tetrahydrofuran / 2 h / 25 °C View Scheme