Multi-step reaction with 12 steps
1.1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C
2.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0.17 h / 20 °C
2.2: 0.67 h / 20 °C
3.1: tetrabutylammomium bromide; palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere
4.1: methanesulfonamide / water; tert-butyl alcohol / 240 h / 20 °C
5.1: thionyl chloride; triethylamine / dichloromethane / 0.5 h / 0 °C
6.1: sodium azide; tetrabutylammomium bromide / N,N-dimethyl-formamide / 19 h / 90 °C
7.1: toluene-4-sulfonic acid / 3 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C
9.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 20 °C
11.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C
12.1: mercaptoacetic acid; lithium hydroxide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C
With
dmap; lithium aluminium tetrahydride; thionyl chloride; sodium azide; tributylphosphine; methanesulfonamide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; toluene-4-sulfonic acid; mercaptoacetic acid; triethylamine; tris-(o-tolyl)phosphine; sodium hydroxide; lithium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
3.1: Heck reaction / 4.1: Sharpless dihydroxylation;
DOI:10.1002/anie.201106205