Multi-step reaction with 13 steps
1.1: 91 percent / p-toluenesulfonic acid / dimethylformamide / 6 h / 23 °C
2.1: lithium hexamethyldisilazide / toluene / 0.42 h / -78 °C
2.2: 5.55 g / toluene / 0.67 h / -78 °C
3.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C
4.1: 92 percent / 4-dimethylaminopyridine; triethylamine / CH2Cl2 / 0 - 23 °C
5.1: 90 percent / p-toluenesulfonic acid / acetone / 0.25 h / 23 °C
6.1: 88 percent / 2,6-lutidine / CH2Cl2 / 0.33 h / -78 °C
7.1: 94 percent / diisobutylaluminum hydride / toluene; CH2Cl2 / 0.17 h / -78 °C
8.1: (+)-diethyl-L-tartrate; titanium(IV) isopropoxide / CH2Cl2 / 0.5 h
8.2: 98 percent / tert-butyl hydroperoxide / CH2Cl2 / 15 h
9.1: 97 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0.67 h / 23 °C
10.1: 85 percent / 1,3-diphenyl-1,1,3,3-tetramethyldisilazine; n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C
11.1: 89 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C
12.1: 100 percent / Et3N*3HF / tetrahydrofuran / 2.5 h / 23 °C
13.1: tetrahydrofuran / 0.25 h / -10 °C
13.2: DCC / 0.17 h / -10 °C
13.3: n-propylamine / 0.17 h / -10 °C
With
pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; n-butyllithium; diethyl L-tartrate; 1,1,3,3-tetramethyl-1,3-diphenyldisilazane; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine tris(hydrogen fluoride); triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ja012487x