Multi-step reaction with 18 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 20 °C / Inert atmosphere
2.1: osmium(VIII) oxide; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; sodium hydrogencarbonate; potassium carbonate; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 6 h / 5 °C / Inert atmosphere
3.1: nitrogen; methylamine / water / 1 h / 50 °C / 10 Torr / Inert atmosphere
4.1: sodium hydrogencarbonate / ethyl acetate / 1.5 h / Inert atmosphere
5.1: dmap; triethylamine; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.03 h / 0 - 20 °C / Inert atmosphere
6.1: dichloromethane / 1 h / -40 °C / Inert atmosphere
7.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / Inert atmosphere
9.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
10.1: acetic acid / chloroform / 12 h / 20 °C / Molecular sieve; Inert atmosphere
11.1: sodium cyanoborohydride / tetrahydrofuran / 2 h / Inert atmosphere
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
13.1: dmap; potassium carbonate / dichloromethane / 20 °C / Inert atmosphere
14.1: 1,4-diaza-bicyclo[2.2.2]octane; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine / tetrahydrofuran / 20 °C / Inert atmosphere
15.1: palladium diacetate; silver nitrate; triphenylphosphine / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
16.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C / Inert atmosphere
16.2: 2 h / aq. phosphate buffer
17.1: dichloromethane / 1 h / 0 °C / Inert atmosphere
18.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; PhI(OPiv)2; magnesium oxide / 1,2-dichloro-ethane / 20 - 60 °C / Inert atmosphere
With
1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; dmap; osmium(VIII) oxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); methanesulfonamide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; PhI(OPiv)2; nitrogen; tetrabutyl ammonium fluoride; palladium diacetate; magnesium oxide; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; silver nitrate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; methylamine; (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine; potassium hexacyanoferrate(III);
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.201003489