Multi-step reaction with 14 steps
1.1: triethylamine / dichloromethane / 1 h / -78 °C
2.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene; methyloxirane / 168 h / 195 °C / Inert atmosphere
3.1: diethylzinc / hexane / 0.08 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 °C / Inert atmosphere
4.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / -30 - 20 °C
5.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C
5.2: 24 h / 50 °C
6.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium; diethylaluminium chloride / hexane; toluene; benzene / 0.5 h / 0 °C
7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; p-benzoquinone / dichloromethane / 0.33 h / Reflux
8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 36 h / 20 °C / Inert atmosphere
9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0 °C / Molecular sieve; Inert atmosphere
10.1: pyridine hydrogenfluoride / acetonitrile / 24 h / 0 - 20 °C / Inert atmosphere
11.1: sodium hydroxide / 1,4-dioxane; water / 6 h / 90 °C / Inert atmosphere
12.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / -65 - 20 °C
13.1: manganese(IV) oxide / chloroform / 72 h / 20 °C
14.1: dmap / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere
With
2,2,6,6-tetramethyl-piperidine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; tetrapropylammonium perruthennate; cerium(III) chloride heptahydrate; 2,6-di-tert-butyl-4-methyl-phenol; diethylzinc; diethylaluminium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; chloroform; water; toluene; acetonitrile; methyloxirane; mineral oil; benzene;
DOI:10.1021/jo3008034