Multi-step reaction with 8 steps
1: triphenylphosphine; tetrachloromethane / 24 h / 80 °C / Inert atmosphere
2: (DHQD)2PHAL; methanesulfonamide; potassium osmate(VI) dihydrate; potassium hexacyanoferrate(III); potassium carbonate; sodium hydrogencarbonate / tert-butyl alcohol; water / 4 h / 0 °C / Inert atmosphere
3: sodium hydroxide / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
4: 1H-imidazole / dichloromethane / 14 h / 0 - 20 °C / Inert atmosphere
5: copper(l) iodide / tetrahydrofuran; diethyl ether / 1 h / -78 - 20 °C / Inert atmosphere
6: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 6 h / 40 °C / Inert atmosphere
7: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl) / tetrahydrofuran / 50 °C / Inert atmosphere
8: triethylamine / methanol / 0.75 h / 20 °C / Inert atmosphere
With
(DHQD)2PHAL; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrachloromethane; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium osmate(VI) dihydrate; copper(l) iodide; methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; sodium hydroxide; potassium hexacyanoferrate(III);
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;
2: |Sharpless Dihydroxylation;
DOI:10.1021/ol302409g