Multi-step reaction with 13 steps
1.1: iodine; lead(IV) tetraacetate; calcium carbonate / cyclohexane / 2 h / Reflux; Irradiation
2.1: Jones reagent / acetone / 0 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 120 °C
4.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); cyclohexane-1,2-epoxide / tetrachloromethane / 1 h / Reflux
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / 0 - 50 °C
6.1: ozone / dichloromethane / 0.6 h / -78 °C
6.2: 24 h / 20 °C / Inert atmosphere
7.1: [bis(acetoxy)iodo]benzene; iodine / cyclohexane / 1 h / Irradiation
8.1: pyridinium p-toluenesulfonate / 20 - 130 °C
9.1: methanol; triethylamine / 14 h / 50 °C
10.1: triethylamine / dichloromethane / 3 h / 0 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
12.1: oxygen; 5,15,10,20-tetraphenylporphyrin / dichloromethane / 0.5 h / 0 °C / Irradiation
13.1: ferrous(II) sulfate heptahydrate; iodine / methanol / 1 h / 20 °C / Inert atmosphere
13.2: 2 h / 80 °C
With
methanol; ferrous(II) sulfate heptahydrate; lithium aluminium tetrahydride; Jones reagent; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; iodine; oxygen; lead(IV) tetraacetate; pyridinium p-toluenesulfonate; 5,15,10,20-tetraphenylporphyrin; cyclohexane-1,2-epoxide; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; calcium carbonate;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; cyclohexane; acetone; toluene;
12.1: Schenck ene reaction;
DOI:10.1002/anie.201101893