Multi-step reaction with 6 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
1.2: 1.5 h / 0 - 20 °C / Inert atmosphere
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 20 °C / Inert atmosphere
2.2: Ohira-Bestmann reagent / 20 °C / Inert atmosphere
3.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 50 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 5.5 h / 20 °C / Inert atmosphere
6.2: 2 h / 20 °C / Inert atmosphere
With
1H-imidazole; dmap; ethylmagnesium bromide; tetrabutyl ammonium fluoride; acetic acid; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2012.12.014