Multi-step reaction with 10 steps
1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
1.2: 2 h / 0 - 20 °C / Inert atmosphere
2.1: acetyl chloride / methanol / 0.5 h / Inert atmosphere
3.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / dichloromethane; hexane / 3.5 h / -78 - 20 °C / Inert atmosphere
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere
5.2: 3 h / 0 - 20 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.42 h / 20 °C / Inert atmosphere
7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 40 °C / Inert atmosphere
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
8.2: 3 h / 20 °C / Inert atmosphere
8.3: 1 h / 20 °C / Inert atmosphere
9.1: iodonium dicollidine perchlorate / dichloromethane / 16 h / 20 °C / Inert atmosphere
10.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 1 h / 80 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; benzene;
DOI:10.1021/ol5002686