Multi-step reaction with 9 steps
1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 20 °C
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate; N-chloro-succinimide / dichloromethane; water / 12 h / 20 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
3.2: 2 h / 0 - 20 °C / Inert atmosphere
4.1: acetyl chloride / methanol / 0.5 h / Inert atmosphere
5.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / dichloromethane; hexane / 3.5 h / -78 - 20 °C / Inert atmosphere
7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere
7.2: 3 h / 0 - 20 °C / Inert atmosphere
8.1: sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.42 h / 20 °C / Inert atmosphere
9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 40 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl-ammonium chloride; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ol5002686