Multi-step reaction with 11 steps
1.1: lithium diisopropyl amide / -40 °C / Inert atmosphere
2.1: camphor-10-sulfonic acid / toluene / Inert atmosphere
3.1: hydrogen; palladium on activated charcoal / methanol / Inert atmosphere
4.1: sodium hydroxide; water / ethanol / Reflux; Inert atmosphere
5.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
6.1: 20 °C / Inert atmosphere
7.1: Horse Liver Acetone Powder / N,N-dimethyl-formamide / 96 h / 25 °C / Resolution of racemate; Inert atmosphere
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
9.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere
10.1: sodium iodide / acetonitrile / 12 h / Inert atmosphere; Reflux
11.1: lithium hydride / N,N-dimethyl acetamide / 1 h / 60 °C / Inert atmosphere
11.2: 48 h / 60 °C / Inert atmosphere
With
lithium aluminium tetrahydride; oxalyl dichloride; Horse Liver Acetone Powder; palladium on activated charcoal; camphor-10-sulfonic acid; water; hydrogen; lithium hydride; triethylamine; N,N-dimethyl-formamide; sodium iodide; sodium hydroxide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; acetonitrile;
1.1: |Aldol Addition;
DOI:10.1021/acs.oprd.5b00396