Multi-step reaction with 10 steps
1.1: potassium carbonate / water / 2.5 h / 20 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 °C / Inert atmosphere
2.2: 2 h / 0 °C / Inert atmosphere
3.1: triethylsilane; trifluoroacetic acid / dichloromethane / 0.58 h / 20 °C / Inert atmosphere
4.1: triethylamine / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere
4.2: 1 h / 0 °C / Inert atmosphere
5.1: dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere
6.1: tris-(dibenzylideneacetone)dipalladium(0); (R,R)-ANDEN-phenyl Trost ligand / diethyl ether / 7 h / -25 °C / Inert atmosphere
7.1: dimethyl sulfoxide; acetic acid; hydrogenchloride / water / 2 h / 25 °C / Inert atmosphere
8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 - 25 °C / Inert atmosphere
8.2: 0 - 25 °C / Inert atmosphere
9.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / dichloromethane; water / 25 °C / Inert atmosphere
10.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C / Inert atmosphere
With
hydrogenchloride; triethylsilane; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); osmium(VIII) oxide; (R,R)-ANDEN-phenyl Trost ligand; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/chem.201502878