Multi-step reaction with 24 steps
1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
2: Grubbs' dihydroimidazoline ruthenium catalyst / dichloromethane / Heating
3: potassium dioxotetrahydroxoosmate(VI); sodium hydrogencarbonate; potassium hexacyanoferrate(III) / methanesulfonamide; potassium carbonate / tert-butyl alcohol / 20 °C
4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C
5: sodium hydride / tetrahydrofuran / Heating
6: lithium borohydride / tetrahydrofuran / Heating
7: 2,6-dimethylpyridine; dmap / dichloromethane / 20 °C
8: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
9: Quinuclidine; potassium dioxotetrahydroxoosmate(VI); potassium hexacyanoferrate(III) / methanesulfonamide; potassium carbonate / tert-butyl alcohol / 20 °C
10: potassium carbonate / methanol / 20 °C
11: N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve / acetonitrile / 20 °C
12: amberlyst-15 / 20 °C
13: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
14: N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve / dichloromethane / 20 °C
15: triethylamine / N,N-dimethyl-formamide / 120 °C
16: 3,3-dimethyldioxirane / dichloromethane; acetone / 0 °C
17: triethylamine / N,N-dimethyl-formamide / 150 °C
18: Phenylselenyl bromide / dichloromethane / 0 - 20 °C
19: sodium tetrahydroborate / methanol / 0 °C
20: 2,4,6-trichlorobenzoyl chloride / toluene / 80 °C
21: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
22: PS-TsOH / dichloromethane / 20 °C
23: hydrogenchloride / methanol / 40 °C
24: dmap / dichloromethane / 20 °C
With
Quinuclidine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; amberlyst-15; potassium dioxotetrahydroxoosmate(VI); 4 A molecular sieve; PS-TsOH; Phenylselenyl bromide; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III);
methanesulfonamide; Grubbs' dihydroimidazoline ruthenium catalyst; potassium carbonate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol;
5: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/anie.200353140