Multi-step reaction with 12 steps
1: triphenylphosphine; diethylazodicarboxylate / toluene / 18 h / -30 °C
2: sodium hydroxide / tetrahydrofuran; methanol; water / 0.5 h / 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane; toluene / 3.5 h / 90 °C
4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C
5: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydroxide / tetrahydrofuran / 2 h / 20 °C
6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -30 - -10 °C
7: potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 0.33 h / 170 °C
8: pyridine hydrogenfluoride / acetonitrile / 1 h / 20 °C
9: sulphamoyl chloride / N,N-dimethyl acetamide; acetonitrile / 0.25 h / 20 °C
10: dirhodium tetraacetate; [bis(acetoxy)iodo]benzene; magnesium oxide / dichloromethane / 1 h / 40 °C
11: dmap; triethylamine / tetrahydrofuran / 1.5 h / 20 °C
12: water; sodium hydride / tetrahydrofuran; mineral oil / 0 °C
With
dmap; dirhodium tetraacetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; [bis(acetoxy)iodo]benzene; sulphamoyl chloride; tetrabutyl ammonium fluoride; water; magnesium oxide; sodium hydride; potassium carbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; N,N-dimethyl acetamide; water; toluene; acetonitrile; mineral oil;
1: Mitsunobu reaction / 5: Suzuki-Miyaura coupling / 7: Overman rearrangement;
DOI:10.1021/ol300431n