Multi-step reaction with 12 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / Reflux
2.1: sodium hydroxide / 1,4-dioxane; water / 2 h / 20 °C
2.2: 0.5 h / 20 °C / pH 7
3.1: pyridine / dichloromethane / 14 h / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 14 h / 20 °C
4.2: 15 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
6.2: 1.5 h / 0 - 20 °C / Inert atmosphere
7.1: Triphenylsilyl chloride; dmap; triethylamine / acetonitrile / 2 h / 20 °C
7.2: 1 h
8.1: palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
9.1: silver nitrate; 2,4,6-trimethyl-pyridine / dichloromethane / 20 °C / Inert atmosphere
10.1: 1H-tetrazole / acetonitrile / 1 h / 20 °C / Inert atmosphere
10.2: TBDPH / 1 h
11.1: ammonia / methanol / 2 h / 20 °C
12.1: pyridine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; 1H-tetrazole; 2,4,6-trimethyl-pyridine; dmap; n-butyllithium; Triphenylsilyl chloride; palladium on activated charcoal; ammonia; hydrogen; Dess-Martin periodane; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;