Multi-step reaction with 13 steps
1.1: sodium hydride / tetrahydrofuran / 2.58 h / 0 - 20 °C / Inert atmosphere
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 5 h / 20 °C / Inert atmosphere
3.1: benzene / 3 h / 80 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / 0 °C / Inert atmosphere
4.2: 0 °C / Inert atmosphere
5.1: pyridinium p-toluenesulfonate / dichloromethane / 6 h / 0 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.5 h / 20 °C / Inert atmosphere
7.1: trimethylamine hydrochloride; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
8.1: sodium iodide / acetone / 8.5 h / Inert atmosphere; Reflux
9.1: tert.-butyl lithium / diethyl ether; pentane / 0.25 h / -78 °C / Inert atmosphere
9.2: -78 - 0 °C / Inert atmosphere
9.3: 0 °C / Inert atmosphere
10.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere; Molecular sieve
11.1: pyridinium p-toluenesulfonate / methanol / 5 h / 20 °C / Inert atmosphere
12.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 18 h / -20 °C / Molecular sieve; Inert atmosphere
12.2: -20 °C / Inert atmosphere
13.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran; acetonitrile / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrapropylammonium perruthennate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; diethyl (2S,3S)-tartrate; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; trimethylamine hydrochloride; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; acetonitrile; pentane; benzene;
3.1: Wittig reaction / 12.1: Sharpless asymmetric epoxidation;
DOI:10.1038/ja.2011.90