Multi-step reaction with 14 steps
1.1: (1R,2R)-3-tert-butyldimethylsilyloxy-2-(N,N-dimethylamino)-1-p-nitrophenyl-1-propanol; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.5 h / 55 °C / Inert atmosphere
1.2: 46 h / 55 °C / Inert atmosphere
2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 20 h / -78 - 40 °C / Inert atmosphere
2.2: 0 °C / Inert atmosphere
3.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 48 h / 40 °C / Inert atmosphere
4.1: di(rhodium)tetracarbonyl dichloride / toluene / 50 h / 90 °C / 760.05 Torr
5.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 12 h / 25 °C / Inert atmosphere
5.2: -10 - 20 °C / Inert atmosphere
6.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 2 h / 0 °C / Inert atmosphere
7.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium; dimethylaluminum chloride / hexane; n-heptane; benzene / 2 h / 0 °C / Inert atmosphere
7.2: Inert atmosphere
8.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 50 °C / Inert atmosphere
8.2: 5 h / 50 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 21 h / 40 °C / Inert atmosphere
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 25 °C / Inert atmosphere
11.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere
11.2: 0 °C / Inert atmosphere
12.1: pyridine; dmap / tetrahydrofuran; benzene / 3 h / 30 °C / Inert atmosphere
12.2: 16 h / 30 °C / Inert atmosphere
13.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 3.5 h / 90 °C / Reflux; Inert atmosphere
14.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C / Inert atmosphere
14.2: Inert atmosphere
With
pyridine; 2,2,6,6-tetramethyl-piperidine; 1H-imidazole; dmap; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; di(rhodium)tetracarbonyl dichloride; (1R,2R)-3-tert-butyldimethylsilyloxy-2-(N,N-dimethylamino)-1-p-nitrophenyl-1-propanol; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; dimethylaluminum chloride; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; hexane; n-heptane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1039/c1cc11005e