Multi-step reaction with 12 steps
1: D-(-)-DIPT, TBHP, Ti(O-i-Pr)4 / CH2Cl2 / -20 °C
2: Et3N, DMAP / CH2Cl2
3: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C
4: 94 percent / pyridine / CH2Cl2 / Ambient temperature
5: NaN3 / dimethylformamide / 7 h / 80 °C
6: 2N aq. HCl / 0.5 h
7: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
8: 89 percent / imidazole / dimethylformamide / 0 °C
9: pyridine / CH2Cl2 / 2 h / Ambient temperature
10: pyridine / 4 h / Ambient temperature
11: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
12: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
With
pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; copper(l) iodide; osmium(VIII) oxide; sodium azide; tetrabutyl ammonium fluoride; water; potassium carbonate; (1R)-((1S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl 4-chlorobenzoate; D-(-)-diisopropyl tartrate; triethylamine; lithium bromide; potassium hexacyanoferrate(III);
In
tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/0957-4166(95)00383-5