Multi-step reaction with 9 steps
1.1: di(rhodium)tetracarbonyl dichloride / toluene / 50 h / 90 °C / 760.05 Torr
2.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 12 h / 25 °C / Inert atmosphere
2.2: -10 - 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 2 h / 0 °C / Inert atmosphere
4.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dimethylaluminum chloride / hexane; n-heptane; benzene / 2 h / 0 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 50 °C / Inert atmosphere
5.2: 5 h / 50 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 21 h / 40 °C / Inert atmosphere
7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 25 °C / Inert atmosphere
8.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere
8.2: 0 °C / Inert atmosphere
9.1: pyridine; dmap / tetrahydrofuran; benzene / 3 h / 30 °C / Inert atmosphere
9.2: 16 h / 30 °C / Inert atmosphere
With
pyridine; 2,2,6,6-tetramethyl-piperidine; dmap; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; di(rhodium)tetracarbonyl dichloride; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; dimethylaluminum chloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; hexane; n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1039/c1cc11005e