Multi-step reaction with 9 steps
1.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux
2.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C
2.2: 12.25 h / 0 - 25 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C
3.2: 1 h / -78 °C
4.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C
5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
5.2: 1.5 h / -78 °C
6.1: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; water / 2 h / 100 °C / Microwave irradiation
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C
8.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 50 °C / 2585.81 Torr
9.1: Daicel IA-H / ethanol; hexanes / 25 °C / Resolution of racemate
With
tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; sodium; sodium carbonate; Dess-Martin periodane; copper(I) bromide; sodium hydroxide; lithium hexamethyldisilazane; lithium diisopropyl amide;
bis-triphenylphosphine-palladium(II) chloride; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexanes; ethanol; dichloromethane; water; N,N-dimethyl-formamide;