Multi-step reaction with 12 steps
1.1: iodine; silver trifluoroacetate / methanol / 72 h / 25 °C
2.1: N-ethyl-N,N-diisopropylamine; copper(l) iodide / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 2 h / 0 - 25 °C
3.1: pyridine / dichloromethane / 12 h / 0 - 25 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C / Reflux
5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C
5.2: 12.25 h / 0 - 25 °C
6.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 - 20 °C
7.1: thionyl chloride / dichloromethane / 2 h / 0 °C
8.1: methanol / 12 h / 20 °C
9.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C
9.2: 12.25 h / 0 - 25 °C
10.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C
10.2: 1 h / -78 °C
11.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C
12.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
12.2: 1.5 h / -78 °C
With
pyridine; copper(l) iodide; n-butyllithium; thionyl chloride; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; silver trifluoroacetate; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hexamethyldisilazane;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;