Multi-step reaction with 15 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.33 h / -78 °C
1.2: 1 h / 20 °C
2.1: copper(II) sulfate / dichloromethane / 22 h / 20 °C
3.1: tetrahydrofuran; dichloromethane / 0.67 h / 20 °C
4.1: hydrogenchloride / methanol; ethyl acetate / 5 h / 20 °C
5.1: sodium carbonate / tetrahydrofuran; water / 12 h / 20 °C
6.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
7.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / tetrahydrofuran; tert-butyl alcohol; water / 14 h / 20 °C
8.1: triethylamine; diphenyl phosphoryl azide / dichloromethane / 17.33 h / 0 - 20 °C
9.1: 29 h / Reflux
10.1: potassium carbonate / methanol / 14 h / 20 °C
11.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
12.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
13.1: triethylamine / dichloromethane / 19 h / 0 - 20 °C
14.1: trifluoroacetic acid; palladium on activated charcoal; hydrogen / tetrahydrofuran / 1 h / 0 °C
15.1: triethylamine / dichloromethane / 1 h / 0 °C
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; diphenyl phosphoryl azide; palladium on activated charcoal; hydrogen; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; Dess-Martin periodane; copper(II) sulfate; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol;
3.1: |Grignard Reaction / 6.1: |Dess-Martin Oxidation / 9.1: |Curtius Rearrangement;
DOI:10.1021/jm400542h