Multi-step reaction with 14 steps
1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.58 h / -78 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C
2.2: 2 h / 0 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
4.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate / toluene / 10 h / 100 °C
5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / benzene / 16 h / 60 °C / Inert atmosphere
6.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; ethanol / 72 h / 20 °C
7.1: pyridinium p-toluenesulfonate / dichloromethane / 3.5 h / 20 °C
8.1: diisobutylaluminium hydride / hexane; dichloromethane / 3.17 h / -40 - 0 °C
9.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C
10.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C
11.1: tetrahydrofuran / 2.5 h / 20 °C
12.1: caesium carbonate / water / 0.25 h / 20 °C
12.2: 10 h / 50 °C
13.1: dimethylsulfide borane complex / tetrahydrofuran / 5 h / 0 - 20 °C
13.2: 2 h / 20 °C
14.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; bis(1,5-cyclooctadiene)diiridium(I) dichloride; tetrapropylammonium perruthennate; dimethylsulfide borane complex; palladium on activated charcoal; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium carbonate; caesium carbonate; 4-methylmorpholine N-oxide; triphenylphosphine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; water; toluene; benzene;
2.1: Wittig reaction / 2.2: Wittig reaction;
DOI:10.1021/ja300565t