Multi-step reaction with 17 steps
1.1: sodium azide; ammonium chloride / DMF (N,N-dimethyl-formamide) / 4 h / Heating / reflux
2.1: hydrogen / palladium(II) hydroxide/carbon / methanol / 3 h / 20 °C / 760.05 Torr
3.1: silver cyanide / benzene / 22 h / 75 °C
4.1: acetyl chloride / methanol / 2.17 h / 0 - 20 °C
4.2: 20 °C / pH 7
5.1: dmap; triethylamine / dichloromethane / 17 h / 0 - 20 °C
6.1: pyridine; dmap / 19.08 h / 20 °C
7.1: sodium iodide / acetone / 24 h / Heating / reflux
8.1: zinc / tetrahydrofuran; water / 3 h / Heating / reflux
9.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 2.5 h / -20 °C
10.1: Hoveyda-Grubbs 2nd-generation catalyst / benzene / 14 h / Heating / reflux
11.1: potassium carbonate / methanol / 13 h / Heating / reflux
12.1: n-butyllithium / tetrahydrofuran; hexanes / 0.28 h / -78 °C
12.2: 4.33 h / -78 - 20 °C / Heating / reflux
12.3: 18 h / Heating / reflux
13.1: dmap; triethylamine / tetrahydrofuran; dichloromethane / 3.5 h / 20 °C
14.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 7 h / Heating / reflux
15.1: lithium hydroxide / tetrahydrofuran; water / 94.5 h / 20 °C
16.1: dipyridinium dichromate / DMF (N,N-dimethyl-formamide) / 1.5 h / 20 °C
17.1: N-Bromosuccinimide / tetrahydrofuran / 7 h / 0 - 20 °C
17.2: 15 h / 20 °C
With
pyridine; dmap; lithium hydroxide; N-Bromosuccinimide; dipyridinium dichromate; n-butyllithium; sodium azide; silver cyanide; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; potassium hexamethylsilazane; potassium carbonate; ammonium chloride; triethylamine; acetyl chloride; sodium iodide; zinc;
Hoveyda-Grubbs 2nd-generation catalyst; palladium(II) hydroxide/carbon;
In
tetrahydrofuran; methanol; hexanes; DMF (N,N-dimethyl-formamide); dichloromethane; water; acetone; toluene; benzene;
8.1: Vasella reductive ring-opening / 9.1: Kocienski's modification of Julia reaction;