Multi-step reaction with 9 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 12 h / 80 °C
2.1: tetrahydrofuran / 12 h / -78 - 20 °C / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C / Cooling with ice
4.1: sulfuric acid / acetic acid / 12 h / 0 - 20 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 0 - 20 °C / Inert atmosphere
5.2: 4 h / 0 - 60 °C
6.1: silver nitrate; 2,3,5-trimethyl-pyridine / dichloromethane / 12 h / 20 °C
7.1: 3-hydroxylacrylic nitrile; sodium hydride / tetrahydrofuran / 12.5 h / 0 - 20 °C
8.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 - 20 °C
8.2: 12 h / -78 - 20 °C
9.1: formic acid / water / 12 h / 20 °C
With
2,3,5-trimethyl-pyridine; dmap; formic acid; sulfuric acid; tert-butylmagnesium chloride; sodium hydride; 3-hydroxylacrylic nitrile; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; dichloromethane; water; acetic acid; acetonitrile;