Multi-step reaction with 13 steps
1.1: sodium hydroxide / water
2.1: methanol; toluene-4-sulfonic acid / 2 h / 70 °C
3.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C
4.2: 0 - 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 20 °C
6.1: sodium hydrogencarbonate; Dess-Martin periodane / 0.25 h / 20 °C
7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
7.2: -78 - 20 °C
8.1: AD-mix-β / water; tert-butyl alcohol / 168 h / 0 °C
9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice bath
9.2: 0 - 20 °C
10.1: methanol; toluene-4-sulfonic acid / 24 h / 20 °C
11.1: thionyl chloride; triethylamine / dichloromethane / 0.75 h / Cooling with ice bath
12.1: sodium periodate / ruthenium trichloride / tetrachloromethane; water; acetonitrile / 2 h / 20 °C
13.1: potassium carbonate / 1,1,1,3',3',3'-hexafluoro-propanol / 168 h / 75 °C / Sealed tube
With
1H-imidazole; methanol; sodium hydroxide; sodium periodate; n-butyllithium; thionyl chloride; AD-mix-β; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine;
ruthenium trichloride;
In
tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol; water; N,N-dimethyl-formamide; acetonitrile; mineral oil; tert-butyl alcohol;