Multi-step reaction with 10 steps
1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 3 h / 20 °C
1.2: 15 h / 20 °C
2.1: 10-camphorsufonic acid / methanol / 1 h / 0 °C
3.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
4.1: tetrahydrofuran / 0.33 h / 20 °C
4.2: 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / 20 °C
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C
8.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
9.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C
9.2: 13.25 h / -78 - 20 °C / Molecular sieve
10.1: water; triethylamine / methanol / 3 h / 20 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,4,6-trichlorobenzoyl chloride; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; water; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; dichloromethane;
1.1: Yamaguchi esterification / 1.2: Yamaguchi esterification / 4.1: Grignard reaction;
DOI:10.1021/jo201158q