Multi-step reaction with 13 steps
1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / -78 - 0 °C / Inert atmosphere
1.2: 13 h / -78 °C / Inert atmosphere
2.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3.1: dicobalt octacarbonyl / toluene / 1.5 h / 20 °C / Inert atmosphere
3.2: 12 h / 100 °C
4.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere
5.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
6.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere
6.2: 0 - 20 °C / Inert atmosphere
7.1: sodium hydrogencarbonate / 1,2-dichloro-benzene / 10 h / 170 °C / Inert atmosphere
8.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere
8.2: -78 - 20 °C / Inert atmosphere
9.1: dimethylsulfide borane complex / tetrahydrofuran; dimethylsulfide / 12.5 h / 0 °C / Inert atmosphere
9.2: 10 h / 0 °C / Inert atmosphere
9.3: NaBO3*4H2O / 4 h / 20 °C / Inert atmosphere
10.1: triethylamine / dichloromethane / 4 h / 0 °C / Inert atmosphere
11.1: dmap / pyridine; dichloromethane / 0 - 20 °C / Inert atmosphere
12.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere
13.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium borohydride; n-butyllithium; dicobalt octacarbonyl; borane-THF; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; pyridine; dimethylsulfide; hexane; dichloromethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; toluene; mineral oil;
3.1: Pauson-Khand reaction / 3.2: Pauson-Khand reaction;
DOI:10.1002/anie.201103550