Multi-step reaction with 14 steps
1.1: quinoline; hydrogen; Lindlar's catalyst / ethyl acetate / 8 h / 23 °C / Inert atmosphere
2.1: camphor-10-sulfonic acid / dichloromethane; methanol / 12 h / 23 °C / Inert atmosphere
3.1: copper(l) iodide / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
3.2: 1 h / 0 °C / Inert atmosphere
3.3: 12 h / 23 °C / Inert atmosphere
4.1: methanol / 10 h / 23 °C / Inert atmosphere
5.1: 1H-imidazole / dichloromethane / 10 h / 23 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
7.1: Dess-Martin periodane / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere
8.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
8.2: 0.5 h / Inert atmosphere
9.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
10.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 12 h / 120 °C / Inert atmosphere
11.1: acetic anhydride; acetic acid; sodium acetate; sodium chromate(VI) / benzene / 12 h / 70 °C / Inert atmosphere
12.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 14 h / 23 °C / Inert atmosphere
13.1: lithium perchlorate / dichloromethane / 5 h / 23 °C / Inert atmosphere
14.1: 3,3-dimethyldioxirane / acetone / 0.17 h / -90 °C / Inert atmosphere
14.2: 12 h / 23 °C / Inert atmosphere
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; quinoline; copper(l) iodide; n-butyllithium; sodium chromate(VI); Lindlar's catalyst; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; lithium perchlorate; 3,3-dimethyldioxirane; acetic anhydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; acetone; toluene; benzene;
7.1: |Dess-Martin Oxidation;
DOI:10.1039/c3ob42049c