Multi-step reaction with 9 steps
1.1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere
2.1: cerium(III) chloride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 °C / Inert atmosphere; Reflux
3.2: 2 h / 0 °C / Inert atmosphere
4.1: dimethylsulfide; ozone / ethyl acetate / 0.5 h / -78 - 0 °C
5.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.5 h / 0 °C / Inert atmosphere
5.2: 3.5 h / 0 °C / Inert atmosphere
6.1: copper(l) cyanide; lithium chloride / tetrahydrofuran; diethyl ether; pentane / 1 h / -78 - 0 °C / Inert atmosphere
7.1: fluorosilicic acid; water / acetonitrile / 14 h / 20 °C
8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 °C / Inert atmosphere
9.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 3 h / 20 °C
With
fluorosilicic acid; cerium(III) chloride; dimethylsulfide; water; copper(l) cyanide; sodium hydride; potassium carbonate; ozone; thiophenol; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate;
In
tetrahydrofuran; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; pentane;
5.1: Horner-Wadsworth-Emmons olefination / 5.2: Horner-Wadsworth-Emmons olefination / 8.1: Mitsunobu reaction;
DOI:10.1021/jm2016914