Multi-step reaction with 14 steps
1.1: potassium carbonate / ethanol; dichloromethane
2.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C
3.1: lithium hydroxide / tetrahydrofuran; water / 2 h
4.1: dmap; triethylamine / dichloromethane / 3 h / Inert atmosphere
5.1: BOP-Cl; triethylamine / acetonitrile / 3 h
6.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h
9.1: Dess-Martin periodane / dichloromethane / 2 h
10.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water / 2 h
10.2: pH 2
11.1: BOP-Cl; triethylamine / acetonitrile / Inert atmosphere
12.1: lithium hydroxide / tetrahydrofuran; water / 2 h / 20 °C
12.2: pH 3
13.1: dichloromethane / 2 h / 20 °C
14.1: diphenyl phosphoryl azide / N,N-dimethyl-formamide / 2 h / 20 °C
With
1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diphenyl phosphoryl azide; BOP-Cl; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hydroxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja110166x