Multi-step reaction with 18 steps
1.1: lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C / Inert atmosphere
1.2: pH 4 / Inert atmosphere
2.1: pivaloyl chloride; triethylamine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -40 °C / Inert atmosphere
3.2: 4 h / -20 °C / Inert atmosphere
4.1: lithium borohydride / tetrahydrofuran; methanol; water / 2.5 h / 0 - 20 °C / Inert atmosphere
4.2: 0 °C / Inert atmosphere
5.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
6.1: water; toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3 h / 0 - 30 °C / 80 Torr
7.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
8.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
9.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere
9.2: Inert atmosphere
10.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 20 °C / Inert atmosphere
12.1: Rh/Al2O3; hydrogen / ethyl acetate / 2 h / 20 °C
13.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere
13.2: 0.5 h / -20 °C / Inert atmosphere
14.1: lithium borohydride / tetrahydrofuran; methanol; water / 1 h / 0 - 20 °C / Inert atmosphere
14.2: 0 °C / Inert atmosphere
15.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
16.1: tetrahydrofuran / 0 °C / Inert atmosphere
16.2: Inert atmosphere
17.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 4 h / 0 °C / Inert atmosphere
18.1: tetrahydrofuran; pentane / 0.33 h / -78 °C / Inert atmosphere
18.2: 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; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; pentane;
3.1: Evans asymmetric alkylation / 10.1: Parikh-Doering oxidation / 11.1: Horner-Wadsworth-Emmons olefination / 13.1: Evans asymmetric alkylation / 15.1: Parikh-Doering oxidation / 16.1: Grignard reaction / 17.1: Parikh-Doering oxidation;
DOI:10.3390/molecules16075422