Multi-step reaction with 12 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.67 h / 0 - 20 °C / aq. phosphate buffer
2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 2,6-di-tert-butyl-4-methyl-phenol; sodium hydroxide / tetrahydrofuran; water / 20 h / 20 °C / Inert atmosphere
3.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.25 h / 0 - 20 °C
4.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 21 h / 20 °C / Inert atmosphere
5.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C
5.2: 0 °C / Saturated solution
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10.5 h / Reflux
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C
7.2: 0 °C / Saturated solution
8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C
9.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
9.2: 3 h / -78 - 0 °C / Inert atmosphere
10.1: camphor-10-sulfonic acid / methanol / 120 h / 40 °C
11.1: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C
12.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 6 h / 0 - 20 °C
With
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 2,6-di-tert-butyl-4-methyl-phenol; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol;
2.1: Suzuki-Miyaura coupling / 3.1: Dess-Martin oxidation / 8.1: Dess-Martin oxidation / 9.2: Horner-Wadsworth-Emmons olefination / 11.1: Dess-Martin oxidation / 12.1: Kraus-Pinnick oxidation;
DOI:10.1016/j.tet.2011.04.006