Multi-step reaction with 10 steps
1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane
2.1: Hoveyda-Grubbs catalyst second generation / 1,1-dichloroethane / 90 °C / Inert atmosphere
3.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / 1,2-dichloro-ethane / Inert atmosphere
4.1: formic acid; palladium diacetate; triethylamine / 1,2-dichloro-ethane / 40 °C / Inert atmosphere
4.2: Inert atmosphere
5.1: lithium aluminium tetrahydride / diethyl ether / Inert atmosphere
6.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere
7.1: pyridine; ozone / methanol; dichloromethane / -78 °C / Inert atmosphere
7.2: Inert atmosphere
8.1: magnesium / diethyl ether / -78 °C / Inert atmosphere
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / Inert atmosphere
10.1: cerium(III) chloride heptahydrate / water; acetonitrile / Inert atmosphere
With
pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; formic acid; Hoveyda-Grubbs catalyst second generation; cerium(III) chloride heptahydrate; 2-nitrobenzenesulfonyl hydrazide; palladium diacetate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; ozone; magnesium; triethylamine;
In
methanol; diethyl ether; 1,1-dichloroethane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/jo2003506