Multi-step reaction with 24 steps
1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane
2: sodium hydride / tetrahydrofuran
3: diisobutylaluminium hydride / tetrahydrofuran
4: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane
5: pyridine; tributylphosphine
6: dichloromethane
7: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide
8: sodium periodate / methanol; water
9: 2,6-dimethylpyridine; trifluoroacetic anhydride / acetonitrile
10: sodium hydride / tetrahydrofuran
11: aluminum oxide; 20 % Pd(OH)2/C; hydrogen / ethanol
12: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane
13: lithium diisopropyl amide / tetrahydrofuran
14: lithium aluminium tetrahydride / tetrahydrofuran
15: 1H-imidazole / dichloromethane
16: tetra-(n-butyl)ammonium iodide; potassium hydride / tetrahydrofuran
17: tetrabutyl ammonium fluoride / tetrahydrofuran
18: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran
19: hydrogenchloride / methanol
20: 2,6-dimethylpyridine / dichloromethane
21: pyridine; pyridine hydrogenfluoride / tetrahydrofuran
22: Dess-Martin periodane / dichloromethane
23: tetrahydrofuran / 0 °C
24: 3-chloro-benzenecarboperoxoic acid / dichloromethane
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; 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; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic anhydride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
1: Swern oxidation / 2: Horner-Emmons olefination / 4: Katsuki-Sharpless epoxidation / 9: Pummerer rearrangement / 10: Horner-Emmons olefination / 22: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2011.10.073