Multi-step reaction with 13 steps
1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0.33 h / 50 °C
2: lithium chloride; lithium diisopropyl amide / tetrahydrofuran / 14 h / -78 - 20 °C
3: ammonia borane; lithium diisopropyl amide / tetrahydrofuran / 4 h / -78 - 20 °C
4: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C
5: diisobutylaluminium hydride / dichloromethane / 2 h / -40 - -10 °C
6: sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1.5 h / 0 - 20 °C
7: sodium hexamethyldisilazane / tetrahydrofuran / 18 h / -78 - 20 °C
8: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 0 - 20 °C
9: sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1.5 h / 0 - 20 °C
10: benzoic acid / toluene / 0.25 h / 90 °C
11: diisobutylaluminium hydride / dichloromethane / 1 h / -78 - 0 °C
12: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane / 6 h / 0 - 20 °C
13: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran / 4 h / 0 - 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; ammonia borane; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; benzoic acid; lithium chloride; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene;
2: Myers alkylation reaction / 7: Wittig reaction / 10: Wittig reaction / 12: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2011.04.008