1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 1.2: 67 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C 2.1: chiral ligand / Pd2(dba)3CHCl3 / dioxane / 10 h / 23 °C 3.1: TBAF / tetrahydrofuran / 0.08 h View Scheme

1: chiral ligand / Pd2(dba)3CHCl3 / dioxane / 10 h / 23 °C 2: TBAF / tetrahydrofuran / 0.08 h View Scheme

1.1: 79 percent / pyridine / CH2Cl2 / 24 h / 0 - 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C 2.2: 67 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C 3.1: chiral ligand / Pd2(dba)3CHCl3 / dioxane / 10 h / 23 °C 4.1: TBAF / tetrahydrofuran / 0.08 h View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran 0.0833333 h;

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide 6 h; Ambient temperature; Yield given;

1: AD-mix-β, OsO4, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 0 °C 2: camphorsulfonic acid / tetrahydrofuran / 1.5 h / Ambient temperature 3: DIBAL-H / tetrahydrofuran; hexane / 14 h / Ambient temperature 4: Zn, Me3Al / tetrahydrofuran / 2 h / -20 - 20 °C 5: 2N aq. HCl / methanol / 4 h / Ambient temperature 6: o-iodoxybenzoic acid / dimethylsulfoxide / 6 h / Ambient temperature View Scheme

1: camphorsulfonic acid / tetrahydrofuran / 1.5 h / Ambient temperature 2: DIBAL-H / tetrahydrofuran; hexane / 14 h / Ambient temperature 3: Zn, Me3Al / tetrahydrofuran / 2 h / -20 - 20 °C 4: 2N aq. HCl / methanol / 4 h / Ambient temperature 5: o-iodoxybenzoic acid / dimethylsulfoxide / 6 h / Ambient temperature View Scheme

1: 17 percent / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 2: 80percent TFA / 24 h / Ambient temperature View Scheme

trifluoroacetic acid 24 h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;