Multi-step reaction with 11 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C / Inert atmosphere
1.2: 12 h / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane; N,N,N,N,N,N-hexamethylphosphoric triamide / 0 °C / Inert atmosphere
2.2: 2 h / 0 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / ethanol / 0.5 h / Inert atmosphere; Reflux
4.1: sodium; ammonia / tetrahydrofuran; tert-butyl alcohol / 1 h / -40 °C / Inert atmosphere
5.1: Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
6.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1.5 h / -25 °C / Inert atmosphere
6.2: 0.33 h / -78 °C / Inert atmosphere
7.1: bis-[(trifluoroacetoxy)iodo]benzene / methanol; water / 0.08 h / Inert atmosphere
8.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.5 h / Inert atmosphere
9.1: caesium carbonate / acetone / 4 h / Inert atmosphere; Reflux
10.1: chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 3 h / 0 °C / Inert atmosphere; Reflux
11.1: tetrakis(triphenylphosphine) palladium(0) / ethanol / 3 h / Inert atmosphere; Reflux
With
tetrakis(triphenylphosphine) palladium(0); n-butyllithium; chloro-trimethyl-silane; carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; ammonia; tert.-butyl lithium; sodium; pyridinium p-toluenesulfonate; caesium carbonate; Dess-Martin periodane; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetone; tert-butyl alcohol; pentane;
DOI:10.1021/jo302353g