Multi-step reaction with 14 steps
1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / 0 - 25 °C / Inert atmosphere
2.1: magnesium / tetrahydrofuran / 16 h / 25 °C / Inert atmosphere
2.2: -78 - 25 °C / Inert atmosphere
2.3: -78 °C
3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / 25 °C / Inert atmosphere
4.1: acetonitrile / 1 h / 0 °C / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 °C / Inert atmosphere
5.2: 0.5 h / 0 °C / Inert atmosphere
5.3: 0 - 25 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere
7.1: sodium periodate / dichloromethane; water / 0.5 h / 25 °C / Inert atmosphere
8.1: triethylamine / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere
9.1: caesium carbonate / 1,4-dioxane / 18 h / 25 - 100 °C / Inert atmosphere
10.1: caesium carbonate / tetrahydrofuran / 20 h / 25 °C / Inert atmosphere
11.1: silver trifluoromethanesulfonate / dichloromethane / 1 h / 25 °C / Inert atmosphere
11.2: -45 - 25 °C
12.1: tert-butyl alcohol / tetrahydrofuran / 0.17 h / 25 °C / Inert atmosphere
12.2: 0.17 h / -78 °C / Inert atmosphere
12.3: -78 - 25 °C / Inert atmosphere
13.1: Schwartz's reagent / tetrahydrofuran / 16 h / 25 - 40 °C / Inert atmosphere
14.1: triethylamine / dichloromethane / 18 h / 25 °C / Inert atmosphere
With
sodium periodate; Schwartz's reagent; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; sulfur trioxide pyridine complex; caesium carbonate; magnesium; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; tert-butyl alcohol;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;