Multi-step reaction with 8 steps
1.1: sodium hydrosulfite pentahydrate; tetrabutylammomium bromide; potassium hydroxide / water; toluene / Cooling with ice; Reflux
2.1: Iodine monochloride / methanol / Cooling with ice; Reflux
3.1: n-butyllithium / diethyl ether; hexane / 0.75 h / 0 °C / Inert atmosphere
3.2: 2 h / 20 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.1: n-butyllithium / diethyl ether; hexane / 0 °C / Inert atmosphere
5.2: 2 h / 20 °C / Inert atmosphere
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / chloroform / 40 h / Inert atmosphere; Reflux
7.1: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate / toluene / 20 h / 80 °C / Inert atmosphere
8.1: toluene-4-sulfonic acid / benzene / 24 h / Reflux
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; sodium hydrosulfite pentahydrate; potassium tert-butylate; tetrabutylammomium bromide; Iodine monochloride; potassium carbonate; toluene-4-sulfonic acid; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; chloroform; water; toluene; benzene;
4.1: Wittig reaction / 7.1: Suzuki coupling / 8.1: Aldol condensation;
DOI:10.1021/ol102398y