Multi-step reaction with 13 steps
1.1: nickel(IV) oxide / hexane / 2 h / Heating
2.1: potassium hydroxide / 1 h / Heating
3.1: thionyl chloride / 4 h / Heating
4.1: dichloromethane / 20 h / 20 °C
5.1: thionyl chloride / 12 h / 20 °C
6.1: silver trifluoromethanesulfonate / benzene / 6 h / Heating
7.1: N-Bromosuccinimide / benzene / 18 h / 25 °C / Irradiation
8.1: potassium carbonate / 1 h / Heating
9.1: thionyl chloride / 6 h / Heating
10.1: triethylamine / dichloromethane / 14 h / 20 °C
11.1: thionyl chloride / 12 h / 20 °C
12.1: silver trifluoromethanesulfonate / benzene / 6 h / Heating
13.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 °C
13.2: 23; 13 / -78 - 20 °C
With
nickel(IV) oxide; potassium hydroxide; N-Bromosuccinimide; thionyl chloride; silver trifluoromethanesulfonate; potassium hexamethylsilazane; potassium carbonate; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; toluene; benzene;
1.1: Dehydrogenation / 2.1: Hydrolysis / 3.1: Substitution / 4.1: Acylation / 5.1: Substitution / 6.1: Cyclization / 7.1: Bromination / 8.1: Hydrolysis / 9.1: Substitution / 10.1: Acylation / 11.1: Substitution / 12.1: Cyclization / 13.1: Metallation / 13.2: Substitution;
DOI:10.1039/b000750L