Multi-step reaction with 9 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.5 h / 20 °C / Inert atmosphere
2.1: trimethylamine hydrochloride; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
3.1: sodium iodide / acetone / 8.5 h / Inert atmosphere; Reflux
4.1: tert.-butyl lithium / diethyl ether; pentane / 0.25 h / -78 °C / Inert atmosphere
4.2: -78 - 0 °C / Inert atmosphere
4.3: 0 °C / Inert atmosphere
5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere; Molecular sieve
6.1: pyridinium p-toluenesulfonate / methanol / 5 h / 20 °C / Inert atmosphere
7.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate / dichloromethane / 18 h / -20 °C / Molecular sieve; Inert atmosphere
7.2: -20 °C / Inert atmosphere
8.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran; acetonitrile / 0 - 20 °C / Inert atmosphere
9.1: sodium iodide; zinc / methanol / 2.5 h / 90 °C / Inert atmosphere
9.2: Inert atmosphere
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; pyridinium p-toluenesulfonate; trimethylamine hydrochloride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium iodide; zinc;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; acetonitrile; pentane;
7.1: Sharpless asymmetric epoxidation;
DOI:10.1038/ja.2011.90