Multi-step reaction with 14 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 90 °C
2.1: 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C
3.1: lithium borohydride / tetrahydrofuran / 3 h / 0 - 20 °C
4.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C
5.1: triethylamine / 12 h
6.1: thionyl chloride / dichloromethane / 1 h / -78 °C
6.2: 1 h / -78 °C
7.1: / acetonitrile / 16 h / 20 °C
8.1: hydrogen / ethanol / 1.5 h / 2585.81 Torr
9.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 - 45 °C
11.1: dmap / dichloromethane / 3 h / 0 °C
12.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C
13.1: sodium periodate / ruthenium(III) trichloride hydrate / 1-methyl-pyrrolidin-2-one; tetrachloromethane; acetonitrile; water / 3.83 h
14.1: ethyl acetate; diethyl ether
With
1H-imidazole; dmap; sodium periodate; lithium borohydride; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; sulfur trioxide pyridine complex; sodium hydride; potassium carbonate; triethylamine;
ruthenium(III) trichloride hydrate;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;