Multi-step reaction with 21 steps
1: magnesium bromide diethyl etherate / dichloromethane / 0 °C
2: 2,6-dimethylpyridine / dichloromethane / 0 °C
3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / pH 7 / aq. buffer
4: Hoveyda-Grubbs catalyst second generation / dichloromethane / 35 °C
5: potassium tert-butylate / tetrahydrofuran / 0 °C
6: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / -60 - -25 °C
7: 10% palladium on activated charcoal; hydrogen / ethyl acetate / 20 °C
8: Dess-Martin periodane / dichloromethane / 20 °C
9: lithium hexamethyldisilazane / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 6 h / -78 - 20 °C
10: potassium hydroxide / tetrahydrofuran; methanol / 60 °C
11: Dess-Martin periodane / dichloromethane / 20 °C
12: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 20 °C
13: methanol / benzene / 20 °C
14: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0 °C
15: potassium trimethylsilonate / diethyl ether / 20 °C
16: triethylamine / tetrahydrofuran / 20 °C
17: dmap / toluene / 80 °C
18: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C
19: Dess-Martin periodane / dichloromethane / 20 °C
20: sodium hexamethyldisilazane / tetrahydrofuran / -40 °C
21: tris-(dibenzylideneacetone)dipalladium(0); triphenyl-arsane; silver(l) oxide / tetrahydrofuran; water / 20 °C
With
2,6-dimethylpyridine; methanol; triethylsilane; dmap; sodium chlorite; tris-(dibenzylideneacetone)dipalladium(0); sodium dihydrogenphosphate; Hoveyda-Grubbs catalyst second generation; magnesium bromide diethyl etherate; 2-methyl-but-2-ene; triphenyl-arsane; 10% palladium on activated charcoal; boron trifluoride diethyl etherate; potassium tert-butylate; potassium trimethylsilonate; hydrogen; sodium hexamethyldisilazane; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide; silver(l) oxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; benzene;
9: Julia Olefin synthesis / 20: Horner-Wadsworth-Emmons olefination / 21: Suzuki coupling;
DOI:10.1002/chem.201003135