Multi-step reaction with 8 steps
1.1: 1H-imidazole / tetrahydrofuran / 1 h / 0 °C
2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 36 h / Inert atmosphere; Reflux
3.1: cerium(III) chloride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere
3.2: -78 - 20 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 3 h / -38 °C / Molecular sieve
5.1: methanesulfonamide / water; tert-butyl alcohol / 1 h / 23 °C / Inert atmosphere
5.2: 0.33 h / 23 °C / Inert atmosphere
6.1: sodium periodate / methanol; water / 2 h / 23 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 23 °C / Inert atmosphere
7.2: 16 h / 40 °C / Inert atmosphere
8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 7 h / Inert atmosphere; Reflux
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium periodate; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; cerium(III) chloride; methanesulfonamide; pyridinium p-toluenesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
4.1: Sakurai reaction / 7.2: Wittig reaction;
DOI:10.1021/ol201626h