Multi-step reaction with 11 steps
1.1: 1H-imidazole / dichloromethane / 0 - 20 °C
2.1: methanol; toluene-4-sulfonic acid / 0 - 20 °C
3.1: sodium tetrahydroborate; nickel diacetate / ethanol; ethylene glycol / 6 h / 20 °C
4.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 12 h / -20 °C / Molecular sieve
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C
5.2: -78 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0 - 20 °C
7.1: scandium tris(trifluoromethanesulfonate) / tetrahydrofuran; water / 12 h / 20 °C
8.1: camphor-10-sulfonic acid / dichloromethane / 0 - 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 4 h / 0 - 20 °C
10.2: 12 h / 0 - 20 °C
11.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Reflux
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium tetrahydroborate; oxalyl dichloride; L-(+)-diisopropyl tartrate; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; nickel diacetate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; scandium tris(trifluoromethanesulfonate);
In
tetrahydrofuran; ethanol; dichloromethane; water; ethylene glycol;
4.1: Sharpless epoxidation / 5.1: Swern oxidation / 5.2: Swern oxidation / 10.1: Yamaguchi reaction / 10.2: Yamaguchi reaction;
DOI:10.1016/j.tetlet.2012.04.118