Multi-step reaction with 11 steps
1.1: sulfuric acid / 12 h / 120 - 125 °C
2.1: potassium carbonate; sodium iodide / acetone / 25 - 30 °C
2.2: 5.5 h / 15 °C / Reflux
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 5 - 10 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 5 °C
5.1: acetonitrile / 32 h / 95 - 100 °C / autoclave; Inert atmosphere
6.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C
7.1: D-tartaric acid / isopropyl alcohol / 16 h / 30 - 35 °C
7.2: 10 - 15 °C
8.1: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave
9.1: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave
10.1: chloroform / 0.75 h / -45 - -35 °C
11.1: D-tartaric acid / isopropyl alcohol / 16 h / 30 - 35 °C
11.2: 10 - 15 °C
With
dmap; n-butyllithium; D-tartaric acid; sulfuric acid; hydrogen; potassium carbonate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide;
5%-palladium/activated carbon;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; isopropyl alcohol; acetone; toluene; acetonitrile;