Multi-step reaction with 16 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere
3.1: sodium hydroxide; dihydrogen peroxide / 16 h / 20 °C / Inert atmosphere
4.1: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: barium carbonate; N-Bromosuccinimide / tetrachloromethane / 2 h / 0 °C / Reflux
6.1: sodium cyanoborohydride; zinc / propan-1-ol; water / 0.67 h / 20 °C / Reflux
7.1: pyridine / 15.5 h / 0 - 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
9.2: 2 h / -78 - 20 °C / Inert atmosphere
10.1: potassium carbonate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
11.1: 2,6-dimethylpyridine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / dichloromethane; toluene / 2.5 h / -78 °C / Inert atmosphere
12.2: 1 h / -78 - 20 °C
13.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
14.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere
14.2: 59 h / 0 °C / Inert atmosphere; Reflux
15.1: triethylamine; tetrakis(triphenylphosphine) palladium(0) / toluene / 1 h / 110 °C / Inert atmosphere
16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; potassium carbonate; triethylamine; barium carbonate; sodium hydroxide; zinc;
In
tetrahydrofuran; methanol; propan-1-ol; tetrachloromethane; hexane; dichloromethane; water; toluene; mineral oil;
DOI:10.1021/ml400098w