Multi-step reaction with 20 steps
1.1: 20 % Pd(OH)2/C; hydrogen / tetrahydrofuran; methanol / 7.5 h / 20 °C
2.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C
3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 0 °C
3.2: 0.67 h / 0 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
5.1: pyridine / 1 h / 0 °C
6.1: silver nitrate; triethylamine / tetrahydrofuran; N,N-dimethyl-formamide / 0.08 h / 0 - 50 °C
6.2: 0.5 h / 0 - 20 °C
7.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C / Inert atmosphere
8.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 0.5 h / 0 °C
9.1: tetrahydrofuran; diethyl ether / 0.67 h / 0 °C
10.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 2 h / 0 - 20 °C / Molecular sieve
11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C
11.2: 4.33 h / -78 - 20 °C
12.1: tetrahydrofuran / 1.75 h / 20 °C
13.1: dihydrogen peroxide; sodium hydrogencarbonate / tetrahydrofuran; water / 2 h / 0 - 20 °C
14.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C
15.1: toluene / 20 h / 100 °C
16.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 h / 20 °C
17.1: diisobutylaluminium hydride / hexane; dichloromethane / 5 h / -78 - -40 °C / Inert atmosphere
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.5 h / 0 - 20 °C
19.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C
20.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrapropylammonium perruthennate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; 20 % Pd(OH)2/C; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; silver nitrate; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja305864z