Multi-step reaction with 10 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 35 - 65 °C / Inert atmosphere
1.2: 3 h / 65 - 70 °C / Inert atmosphere
2.1: sodium hydride / n-heptane; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
2.2: 2.17 h / 0 - 20 °C / Inert atmosphere
3.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / tetrahydrofuran; ethanol / 65 h / 2 °C / Inert atmosphere
3.2: Inert atmosphere
4.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
5.1: AD-mix-α; methanesulfonamide / tetrahydrofuran; water; tert-butyl alcohol / 96 h / -1 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
7.1: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 1 h / 65 °C / Inert atmosphere
8.1: potassium carbonate; water / methanol / 24 h / 20 °C / Inert atmosphere
9.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C / Inert atmosphere
10.1: aluminum isopropoxide; isopropyl alcohol / toluene / 1 h / Inert atmosphere; Reflux
With
1H-imidazole; sodium tetrahydroborate; methanesulfonamide; cerium(III) chloride heptahydrate; AD-mix-α; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; aluminum isopropoxide; sodium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; isopropyl alcohol;
In
tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol;
2.1: |Aldol Condensation / 2.2: |Aldol Condensation / 5.1: |Sharpless Dihydroxylation;
DOI:10.1016/j.tetasy.2013.02.012