Multi-step reaction with 9 steps
1.1: oxygen; ozone / dichloromethane / 0.07 h / -78 °C
1.2: 3 h / -78 - 20 °C
1.3: -78 - 20 °C
2.1: RuBr2{(R)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl}; hydrogen / ethanol / 44 h / 45 °C / 30003 Torr / High-pressure bomb
3.1: lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C
4.1: 2,6-dimethylpyridine / dichloromethane / 22 h / 0 - 20 °C / Inert atmosphere
4.2: 2 h
5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 6 h / 20 °C / Inert atmosphere
5.2: 1.5 h / 20 °C / Inert atmosphere
6.1: pyridine hydrogenfluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere
7.1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; cesium fluoride / 1,4-dioxane / 2 h / 60 °C / Inert atmosphere
8.1: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 0.25 h / 20 °C
9.1: 3-chloro-benzenecarboperoxoic acid / acetonitrile / 7 h / 20 °C
With
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; RuBr2{(R)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl}; 2,4,6-trichlorobenzoyl chloride; hydrogen; oxygen; palladium diacetate; lithium triethylborohydride; pyridine hydrogenfluoride; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; cesium fluoride;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; toluene; acetonitrile;
1.3: Roskamp rearrangement / 7.1: Suzuki coupling / 9.1: Baeyer-Villiger oxidation;
DOI:10.1016/j.tet.2011.09.058