Multi-step reaction with 15 steps
1.1: hydrogen / ethanol / 20 °C
2.1: lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C / Inert atmosphere
2.2: pH 4 / Inert atmosphere
3.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -40 °C / Inert atmosphere
4.2: 4 h / -20 °C / Inert atmosphere
5.1: lithium borohydride / tetrahydrofuran; methanol; water / 2.5 h / 0 - 20 °C / Inert atmosphere
5.2: 0 °C / Inert atmosphere
6.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
7.1: water; toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3 h / 0 - 30 °C / 80 Torr
8.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
9.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
10.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere
10.2: Inert atmosphere
11.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
12.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 20 °C / Inert atmosphere
13.1: Rh/Al2O3; hydrogen / ethyl acetate / 2 h / 20 °C
14.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere
14.2: 0.5 h / -20 °C / Inert atmosphere
15.1: lithium borohydride / tetrahydrofuran; methanol; water / 1 h / 0 - 20 °C / Inert atmosphere
15.2: 0 °C / Inert atmosphere
With
pyridine; 1H-imidazole; lithium borohydride; Rh/Al2O3; water; hydrogen; sulfur trioxide pyridine complex; pivaloyl chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
4.1: Evans asymmetric alkylation / 11.1: Parikh-Doering oxidation / 12.1: Horner-Wadsworth-Emmons olefination / 14.1: Evans asymmetric alkylation;
DOI:10.3390/molecules16075422