Multi-step reaction with 15 steps
1.1: trifluoromethylsulfonic anhydride; 2,6-di-tert-butyl-4-methylpyridine / dichloromethane
2.1: lithium naphthalenide / tetrahydrofuran / 1 h / -40 °C
3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
4.1: hydrogenchloride / tetrahydrofuran; water / 1.5 h / 20 - 50 °C
4.3: CSA / 0.17 h / 90 °C
5.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 18 h / 20 °C
6.1: tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 1 h / 20 °C
7.1: triethylamine / dichloromethane / 0.5 h / 0 °C
8.1: titanium(IV) isopropylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 12 h / 85 °C
9.1: hydrogenchloride / acetone / 3 h / Reflux
10.1: potassium hexamethylsilazane / tetrahydrofuran / -50 °C
10.2: 0 °C
11.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 20 °C / 760.05 Torr
12.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / methanol / 12 h / -78 °C
13.1: triethylamine / dichloromethane / 3 h / 20 °C
14.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C
15.1: palladium 10% on activated carbon; hydrogen / 760.05 Torr
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-4-methylpyridine; samarium diiodide; oxalyl dichloride; trifluoromethylsulfonic anhydride; palladium 10% on activated carbon; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;
3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1021/jo302362b