Multi-step reaction with 11 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C
2.2: 1.08 h / 0 - 20 °C
2.3: 0 °C
3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; ethanol / 5.08 h / -40 - 0 °C
4.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C
5.1: AD-mix-α; methanesulfonamide; water / tetrahydrofuran; tert-butyl alcohol / 16 h / 0 - 20 °C
6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 0 °C
7.1: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 2 h / 65 °C
8.1: methanol; ammonia / 48 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane; water / 2 h
10.1: aluminum isopropoxide; isopropyl alcohol / toluene / 1 h / 100 °C
11.1: sodium hydride / N,N-dimethyl-formamide; mineral oil
11.2: 2.5 h
With
1H-imidazole; methanol; sodium tetrahydroborate; methanesulfonamide; cerium(III) chloride heptahydrate; AD-mix-α; tetrabutyl ammonium fluoride; ammonia; water; pyridinium p-toluenesulfonate; aluminum isopropoxide; sodium hydride; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; isopropyl alcohol;
In
tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol;
5.1: Sharpless dihydroxylation / 10.1: Meerwein-Ponndorf-Verley reduction;
DOI:10.1016/j.tetlet.2012.01.054