Multi-step reaction with 7 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / acetonitrile / 2 h / 20 °C / Inert atmosphere
2.1: pyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine / acetonitrile / 18 h / 80 °C / Inert atmosphere
4.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 16 h / 80 °C / Inert atmosphere
5.1: n-butyllithium / hexane; toluene / 1 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 °C / Inert atmosphere
6.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere
6.2: 2 h / 0 °C / Inert atmosphere
7.1: 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
7.2: 0.08 h / 20 °C / Inert atmosphere
With
pyridine; potassium phosphate; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; borane-THF; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; acetonitrile; mineral oil;
4.1: Suzuki coupling / 6.1: Horner-Wadsworth-Emmons olefination / 6.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2012.04.008