Multi-step reaction with 13 steps
1.1: dichloromethane / 24 h / 25 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -30 °C / Inrtert atmosphere
3.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 25 °C
4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide / tetrahydrofuran / 0.33 h / -20 °C
4.2: 0.5 h / -20 - 25 °C
5.1: hydrogenchloride / 72 h / 120 °C / Inert atmosphere; Molecular sieve
6.1: pyridine / 6 h / 25 °C
7.1: 2 h / 180 °C / vacuum
8.1: tetrahydrofuran / 0.5 h / -30 °C
9.1: potassium hexamethylsilazane / diethylene glycol dimethyl ether; toluene / 1 h / 95 °C / Inert atmosphere
10.1: tetramethylammonium borohydride / tetrahydrofuran; water / 0.5 h / 0 °C
11.1: potassium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 25 °C
11.2: 1.5 h / 25 °C
12.1: tetrabutyl ammonium fluoride; water / tetrahydrofuran; N,N-dimethyl-formamide / 5 h / 65 °C
13.1: potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate / methanol; water / 8 h / 25 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; samarium diiodide; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; tetramethylammonium borohydride; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium hydrogencarbonate;
In
tetrahydrofuran; methanol; dichloromethane; diethylene glycol dimethyl ether; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/ol201095b