Multi-step reaction with 12 steps
1.1: zinc trifluoromethanesulfonate; acetic acid / 48 h / 80 °C
1.2: 1 h / 0 - 20 °C
2.1: dmap; triethylamine / dichloromethane / 4 h / 0 - 20 °C
3.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere
4.1: ytterbium(III) triflate / toluene / 9 h / 20 - 80 °C
5.1: hydrogenchloride; water / tetrahydrofuran / 14 h / 0 - 20 °C
6.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
7.1: CSA / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: pyrographite; triethylamine / tetrahydrofuran / 0.25 h / -46 °C / Inert atmosphere
9.1: -46 - 20 °C
10.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere
11.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone / 2 h / 20 °C
12.1: sodium periodate / tetrahydrofuran; water / 3 h / 20 °C
With
pyridine; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; trifluoromethylsulfonic anhydride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; pyrographite; acetic acid; 4-methylmorpholine N-oxide; triethylamine; ytterbium(III) triflate;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/anie.201008079