Multi-step reaction with 14 steps
1.1: ozone / dichloromethane / -78 °C
2.1: dichloromethane / 2 h / 20 °C
3.1: diisobutylaluminium hydride / dichloromethane / 3 h / 20 °C
4.1: potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 24 h / 0 °C
5.1: dichloromethane / 1 h / 0 °C
6.1: diisobutylaluminium hydride / dichloromethane / 2 h / 20 °C
7.1: triethylamine / dichloromethane / 20 °C
8.1: potassium carbonate / methanol / 1 h / 20 °C
9.1: magnesium / tetrahydrofuran
9.2: 3 h / -35 °C
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C
11.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 24 h / 110 °C
12.1: palladium 10% on activated carbon; hydrogen; sodium carbonate / ethyl acetate
13.1: lithium borohydride / tetrahydrofuran / 2 h / 0 - 20 °C
14.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 20 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium osmate(VI) dihydrate; lithium borohydride; methanesulfonamide; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; ozone; magnesium; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol;
4.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2012.04.030