Multi-step reaction with 18 steps
1.1: selenium(IV) oxide / acetic acid / 12 h / Reflux
2.1: tetrahydrofuran / 0.5 h / 20 °C
3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
4.1: ammonium acetate / 12 h / Reflux
5.1: potassium carbonate / ethanol; dichloromethane
6.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C
7.1: lithium hydroxide / tetrahydrofuran; water / 2 h
8.1: dmap; triethylamine / dichloromethane / 3 h / Inert atmosphere
9.1: BOP-Cl; triethylamine / acetonitrile / 3 h
10.1: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
11.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h
13.1: Dess-Martin periodane / dichloromethane / 2 h
14.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water / 2 h
14.2: pH 2
15.1: BOP-Cl; triethylamine / acetonitrile / Inert atmosphere
16.1: lithium hydroxide / tetrahydrofuran; water / 2 h / 20 °C
16.2: pH 3
17.1: dichloromethane / 2 h / 20 °C
18.1: diphenyl phosphoryl azide / N,N-dimethyl-formamide / 2 h / 20 °C
With
1H-imidazole; dmap; selenium(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diphenyl phosphoryl azide; BOP-Cl; ammonium acetate; 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; acetic acid; N,N-dimethyl-formamide; acetonitrile;
4.1: Bohlmann-Rahtz reaction;
DOI:10.1021/ja110166x