1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 0.33 h / -78 °C 1.3: 6 h / -78 °C 2.1: boron trichloride / n-heptane; dichloromethane / 0.67 h / 0 °C 3.1: water / n-heptane; dichloromethane / 0.33 h / 0 °C 4.1: BOPCl / dichloromethane / 2 h / 20 °C 5.1: dichlorotriphenylphosphorane / pyridine; acetonitrile / 3 h / 20 °C View Scheme

With  pyridine; sodium periodate; osmium(VIII) oxide in  water; tert-butyl alcohol T=20 - 50°C;   

Multi-step reaction with 17 steps 1.1: toluene / 4 h / -40 °C2.1: magnesium / methanol / 2 h / 20 °C3.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 4 h / 20 °C4.1: sodium hydride / tetrahydrofuran; hexane; mineral oil / 0.17 h / 0 °C4.2: 0 - 20 °C5.1: pyridine / dichloromethane / 2 h / 0 °C6.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C7.1: dichloromethane / 1 h / 0 °C8.1: sodium carbonate / tert-butyl benzene / 24 h / 170 °C9.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C10.1: potassium carbonate / tetrahydrofuran; water / 3 h / 0 °C11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C12.1: scandium tris(trifluoromethanesulfonate) / dichloromethane; water / 20 - 40 °C13.1: Jone's reagent / water; acetone / 0 - 20 °C14.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 12 h / 20 °C15.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C16.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 20 - 60 °C17.1: pyridine; sodium periodate; osmium(VIII) oxide / water; tert-butyl alcohol / 20 - 50 °C  

Multi-step reaction with 14 steps 1.1: sodium hydride / tetrahydrofuran; hexane; mineral oil / 0.17 h / 0 °C1.2: 0 - 20 °C2.1: pyridine / dichloromethane / 2 h / 0 °C3.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C4.1: dichloromethane / 1 h / 0 °C5.1: sodium carbonate / tert-butyl benzene / 24 h / 170 °C6.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C7.1: potassium carbonate / tetrahydrofuran; water / 3 h / 0 °C8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C9.1: scandium tris(trifluoromethanesulfonate) / dichloromethane; water / 20 - 40 °C10.1: Jone's reagent / water; acetone / 0 - 20 °C11.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 12 h / 20 °C12.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C13.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 20 - 60 °C14.1: pyridine; sodium periodate; osmium(VIII) oxide / water; tert-butyl alcohol / 20 - 50 °C