Multi-step reaction with 15 steps
1.1: ozone / ethyl acetate / 0.08 h / -78 °C
1.2: 6 h / 25 °C
2.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C
2.2: -78 - 0 °C
3.1: manganese(IV) oxide / dichloromethane / 25 °C
4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 - -20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 25 °C
6.1: pyridine; hydrogen / ethyl acetate / 3 h / 25 °C
7.1: hydrogenchloride; water / tetrahydrofuran / 3 h / 60 °C
8.1: sodium hydride / tetrahydrofuran / 1 h / Reflux
8.2: 4 h / 25 °C
9.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 °C
9.2: 0.5 h / 0 - 25 °C
10.1: sodium tetrahydroborate / ethanol / 1 h / 0 °C
11.1: dmap; triethylamine / dichloromethane / 0.5 h / 0 - 25 °C
12.1: copper(I) iodide-lithium chloride / tetrahydrofuran; diethyl ether / 0.17 h / 25 °C
12.2: 0.5 h / 25 °C
13.1: Jones reagent / acetone / 0.5 h / 25 °C
14.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C
15.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 72 h / 50 °C
With
pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; triethylsilane; dmap; manganese(IV) oxide; sodium tetrahydroborate; Jones reagent; n-butyllithium; copper(I) iodide-lithium chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydride; potassium carbonate; ozone; triethylamine;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1002/asia.201000147