Multi-step reaction with 13 steps
1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C
2.1: cerium(III) chloride / tetrahydrofuran / -78 °C
3.1: potassium carbonate / methanol; water / 50 °C
3.2: 0 °C
4.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / -78 °C
4.2: 65 °C
5.1: ammonium chloride; zinc / ethanol / 160 °C / Microwave irradiation
6.1: pyridinium p-toluenesulfonate / dichloromethane / 40 °C
7.1: N-Bromosuccinimide; sodium hydrogencarbonate; dibenzoyl peroxide / tetrachloromethane; benzene / 70 °C
7.2: 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
9.1: dmap; triethylamine / dichloromethane / 20 °C
10.1: toluene-4-sulfonic acid / methanol; N,N-dimethyl-formamide / 200 °C / Microwave irradiation
11.1: dmap / dichloromethane / 20 °C
12.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / N,N-dimethyl-formamide / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; toluene / 70 °C
With
2,6-dimethylpyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; cerium(III) chloride; trifluoromethylsulfonic anhydride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dibenzoyl peroxide;
In
tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1038/nchem.1074