Multi-step reaction with 13 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.33 h / -78 °C / Inert atmosphere
2.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / Inert atmosphere; Molecular sieve
2.2: 10 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 6 h / -40 - 20 °C / Inert atmosphere
3.2: Saturated solution
4.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 °C / Inert atmosphere
4.2: 19 h / 0 - 60 °C / Inert atmosphere
5.1: methanol; 10-camphorsulfonic acid / 24 h / 20 °C / Inert atmosphere
6.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere
7.1: methanol; 10-camphorsulfonic acid / 1 h / 0 °C / Inert atmosphere
8.1: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; benzene / 1 h / 40 °C / Inert atmosphere
9.1: dimethyl sulfoxide / 3 h / 70 °C / Inert atmosphere
10.1: diisobutylaluminium hydride / hexane; dichloromethane / 2 h / -78 °C / Inert atmosphere
11.1: tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
11.2: Saturated solution
12.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
13.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
13.2: 2 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; titanium(IV) isopropylate; methanol; tetrapropylammonium perruthennate; diethyl (2R,3R)-tartrate; iodine; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; 10-camphorsulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
2.1: Sharpless epoxidation / 2.2: Sharpless epoxidation / 13.2: Wittig reaction;
DOI:10.1016/j.tet.2012.01.071