1.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere 2.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 2.2: 6 h / 20 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 4.1: benzene / 24 h / Inert atmosphere; Reflux 5.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 7.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 8.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 8.2: 15.75 h / 0 - 20 °C / Inert atmosphere 9.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

Multi-step reaction with 3 steps 1: 1.) NaH / 2.) THF, 2 h2: 1.) trifluoroacetic anhydride / 1.) CH2Cl2, 0 deg C, 1 h; 2.) room temp., 4 h3: 1.) NaIO4; 2.) NaHCO3 / 1.) H2O, MeOH, room temp., overnight; 2.) toluene, reflux, 3 h  

Multi-step reaction with 4 steps 1.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere2.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere2.2: 6 h / 20 °C / Inert atmosphere3.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere4.1: benzene / 24 h / Inert atmosphere; Reflux