Multi-step reaction with 19 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
15.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 12 h / 20 °C
16.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
17.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 20 - 60 °C
18.1: pyridine; sodium periodate; osmium(VIII) oxide / water; tert-butyl alcohol / 20 - 50 °C
19.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C
19.2: 0.33 h / -78 °C
19.3: 6 h / -78 °C
With
pyridine; 2,6-dimethylpyridine; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; Jones reagent; n-butyllithium; 2-methyl-but-2-ene; 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; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol;
4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons olefination / 9.1: Overman rearrangement / 15.1: Kraus-Pinnick reaction;
DOI:10.1002/asia.201000602