Multi-step reaction with 10 steps
1.1: 10-camphorsufonic acid / dichloromethane / 2 h / 0 °C
2.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 - 20 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C
4.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C
5.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C
6.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 2 h / 70 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 - 20 °C / pH 7 / aq. phosphate buffer
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane
9.1: potassium hexamethylsilazane / toluene / 0.5 h / 0 °C
9.2: 6 h / -78 - 0 °C
10.1: Zeise's dimer; trans-4-Octene / cyclohexane / 24 h / 70 - 120 °C / Inert atmosphere
With
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; oxalyl dichloride; Zeise's dimer; trans-4-Octene; 10-camphorsufonic acid; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; toluene;
6.1: Sonogashira coupling / 9.1: Wittig reaction / 9.2: Wittig reaction;
DOI:10.1021/ol202104c