Multi-step reaction with 7 steps
1.1: sodium hydrogencarbonate; Dess-Martin periodane; tert-butyl alcohol / dichloromethane / 0.75 h / Inert atmosphere
2.1: 2,6-di-tert-butyl-4-methylpyridine; 1,2-dibromo-1,1,2,2-tetrachloroethane; triphenylphosphine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.2: 3 h / 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 6.08 h / 0 - 20 °C / Inert atmosphere
4.1: barium hydroxide octahydrate / tetrahydrofuran; water / 0.5 h / 20 °C / Inert atmosphere
4.2: 6 h / 20 °C / Inert atmosphere
5.1: (triphenylphosphine)copper(I) hydride hexamer / benzene / 6 h / 20 °C / Inert atmosphere
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 20 °C / pH 7 / Inert atmosphere; aq. buffer
7.1: tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / Inert atmosphere
With
tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-4-methylpyridine; copper(I) thiophene-2-carboxylate; (triphenylphosphine)copper(I) hydride hexamer; barium hydroxide octahydrate; 1,2-dibromo-1,1,2,2-tetrachloroethane; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;
1.1: Dess-Martin oxidation / 4.1: Horner-Wadsworth-Emmons olefination / 4.2: Horner-Wadsworth-Emmons olefination / 7.1: Stille coupling;
DOI:10.1021/ol301103d