Multi-step reaction with 14 steps
1.1: acetic anhydride; dimethyl sulfoxide / 2 h / 50 °C
2.1: toluene / 4 h / -40 °C
3.1: magnesium / methanol / 2 h / 20 °C
4.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / 4 h / 20 °C
5.1: sodium hydride / tetrahydrofuran; hexane; mineral oil / 0.17 h / 0 °C
5.2: 0 - 20 °C
6.1: pyridine / dichloromethane / 2 h / 0 °C
7.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C
8.1: dichloromethane / 1 h / 0 °C
9.1: sodium carbonate / tert-butylbenzene / 24 h / 170 °C
10.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C
11.1: potassium carbonate / tetrahydrofuran; water / 3 h / 0 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
13.1: scandium tris(trifluoromethanesulfonate) / dichloromethane; water / 20 - 40 °C
14.1: Jones reagent / water; acetone / 0 - 20 °C
With
pyridine; Jones reagent; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; acetic anhydride; sodium hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; magnesium; dimethyl sulfoxide; triethylamine; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; methanol; tert-butylbenzene; hexane; dichloromethane; water; acetone; toluene; mineral oil;
4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons olefination / 9.1: Overman rearrangement;
DOI:10.1002/asia.201000602