Multi-step reaction with 7 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere
1.2: 2 h / 0 °C / Inert atmosphere
2.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere
2.2: 0.08 h / 20 °C / Inert atmosphere
3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
4.1: palladium diacetate; sodium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) / 1,2-dimethoxyethane; water / 15 h / 80 °C / Inert atmosphere
5.1: hydrogenchloride / 1,4-dioxane; ethanol / 6 h / 20 °C / Inert atmosphere
6.1: tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 50 °C / Inert atmosphere
7.1: sodium tris(acetoxy)borohydride / tetrahydrofuran; N,N-dimethyl-formamide / 15 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; borane-THF; palladium diacetate; sodium tris(acetoxy)borohydride; sodium hydride; sodium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; toluene; mineral oil;
1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination / 4.1: Suzuki coupling;
DOI:10.1016/j.bmc.2012.04.008