Multi-step reaction with 13 steps
1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 12 h / 50 °C / Inert atmosphere
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
5.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
6.2: 0 - 20 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 50 °C / Inert atmosphere
9.1: propan-1-ol; potassium hydroxide / water / 12 h / Reflux
10.1: sodium carbonate / tetrahydrofuran; water / 3 h / 0 °C
11.1: oxone; Na2EDTA; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate / water; acetonitrile / 3 h / 0 °C
12.1: Dess-Martin periodane / dichloromethane / 20 °C
13.1: tetrahydrofuran / -78 - 0 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; propan-1-ol; oxone; 1,1,1-trifluoro-2-propanone; Na2EDTA; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; potassium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
13.1: Grignard reaction;
DOI:10.1021/ol103094j