Multi-step reaction with 13 steps
1.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
2.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere
3.1: ytterbium(III) triflate / toluene / 9 h / 20 - 80 °C
4.1: hydrogenchloride; water / tetrahydrofuran / 14 h / 0 - 20 °C
5.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
6.1: CSA / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: pyrographite; triethylamine / tetrahydrofuran / 0.25 h / -46 °C / Inert atmosphere
8.1: -46 - 20 °C
9.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere
10.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone / 2 h / 20 °C
11.1: sodium periodate / tetrahydrofuran; water / 3 h / 20 °C
12.1: water; trifluoroacetic acid / acetonitrile / 0.75 h / 0 - 20 °C
13.1: potassium carbonate / ISOPROPYLAMIDE / 1 h / 20 °C / Inert atmosphere
13.2: 0.17 h / 20 °C / Inert atmosphere
With
pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; trifluoromethylsulfonic anhydride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; diisobutylaluminium hydride; potassium carbonate; pyrographite; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; ytterbium(III) triflate;
In
tetrahydrofuran; dichloromethane; ISOPROPYLAMIDE; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1002/anie.201008079