Multi-step reaction with 12 steps
1: 100 percent / Na2S2O4 / H2O; CHCl3 / 1 h / Ambient temperature
2: 80 percent / Et3N / CH2Cl2 / 5 h / 0 °C
3: 87 percent / K2CO3 / acetone / 2 h / Heating
4: 97 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature
5: pyridine / CH2Cl2 / 2 h
6: 80 percent / LiCl, Pd(PPh3)4 / dioxane / 12 h / Heating
7: dihydroquinidine-p-chlorobenzoate, OsO4, K3Fe(CN)6, K2CO3 / 2-methyl-propan-2-ol; H2O / 24 h / Ambient temperature
8: 70 percent / imidazole, dimethylaminopyridine / CH2Cl2 / 3 h / Ambient temperature
9: 91 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
10: 90 percent / NaN3 / dimethylformamide / 4 h / 90 °C
11: Jones reagent / acetone / 2 h / Ambient temperature
12: 73 percent / diethyl ether
With
pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); sodium azide; sodium dithionite; jones reagent; dihydroquinidine 9-O-(4-chlorobenzoate); tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; lithium chloride; potassium hexacyanoferrate(III);
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/0040-4039(93)85034-T