1: 93 percent / DMAP / pyridine / 48 h 2: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C 3: 1.) BBN, 2.) H2O2, NaOAc / 1.) THF, 10 deg C, 2 h, 2.) THF, H2O, 25 deg C, 2 h 4: 92 percent / pyridine View Scheme

1: 93 percent / DMAP / pyridine / 48 h 2: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C 3: 1.) BBN, 2.) H2O2, NaOAc / 1.) THF, 10 deg C, 2 h, 2.) THF, H2O, 25 deg C, 2 h 4: 76 percent / PCC / CH2Cl2 / 20 °C View Scheme

1: 93 percent / DMAP / pyridine / 48 h 2: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C 3: 1.) BBN, 2.) H2O2, NaOAc / 1.) THF, 10 deg C, 2 h, 2.) THF, H2O, 25 deg C, 2 h View Scheme

1: 93 percent / DMAP / pyridine / 48 h 2: 85 percent / CuI / tetrahydrofuran / 2 h / -10 °C View Scheme

chloro(cyclopentadienyl)bis(triphenylphosphinyl) ruthenium(II); triethylammonium hexafluorophosphate in 1,4-dioxane 1 h; Heating;