Multi-step reaction with 19 steps
1: diisobutylaluminium hydride / tetrahydrofuran
2: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane
3: sodium hydride / tetrahydrofuran
4: diisobutylaluminium hydride / tetrahydrofuran
5: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane
6: pyridine; tributylphosphine
7: dichloromethane
8: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide
9: sodium periodate / methanol; water
10: 2,6-dimethylpyridine; trifluoroacetic anhydride / acetonitrile
11: sodium hydride / tetrahydrofuran
12: aluminum oxide; 20 % Pd(OH)2/C; hydrogen / ethanol
13: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane
14: lithium diisopropyl amide / tetrahydrofuran
15: lithium aluminium tetrahydride / tetrahydrofuran
16: 1H-imidazole / dichloromethane
17: tetra-(n-butyl)ammonium iodide; potassium hydride / tetrahydrofuran
18: tetrabutyl ammonium fluoride / tetrahydrofuran
19: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2S,3S)-tartrate; tributylphosphine; di-isopropyl azodicarboxylate; 20 % Pd(OH)2/C; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic anhydride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
2: Swern oxidation / 3: Horner-Emmons olefination / 5: Katsuki-Sharpless epoxidation / 10: Pummerer rearrangement / 11: Horner-Emmons olefination;
DOI:10.1016/j.tetlet.2011.10.073