Multi-step reaction with 15 steps
1: 1.) K2CO3 / 1.) DMF, room t., 24 h, 2.) DMF, 0 deg C, 15 min
2: 53 percent / dimethylformamide / 0.5 h / 0 °C
3: 100 percent / Na2S2O4 / CHCl3; H2O / 0.5 h / Ambient temperature
4: 80 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
5: 90 percent / K2CO3 / acetone / 2 h / 50 °C
6: 80 percent / Bu4NF / tetrahydrofuran / 0.17 h / 0 °C
7: 85 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C
8: 85 percent / LiCl, Pd(Ph3P)4 / 2,6-di-t-butyl-4-methylphenol / dioxane / 1 h / 90 °C
9: 90 percent / dihydroquinine-9-O-phenanthryl ether, OsO4, K2CO3, K3 / 2-methyl-propan-2-ol; H2O / 30 h / Ambient temperature
10: Et3N / CH2Cl2 / 1 h / Ambient temperature
11: 90 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature
12: 65 percent / NaN3 / dimethylformamide / 1 h / 50 °C
13: 70 percent / H2 / PtO2 / ethyl acetate / 14 h / Ambient temperature
14: 65 percent / Bu4NF / tetrahydrofuran / 0.5 h / 0 °C
15: 60 percent / PDC / dimethylformamide / 10 h / Ambient temperature
With
pyridine; osmium(VIII) oxide; dipyridinium dichromate; tetrakis(triphenylphosphine) palladium(0); sodium azide; sodium dithionite; dihydroquinidine 0-O-(9'-phenanthryl) ether; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; triethylamine; lithium chloride; potassium hexacyanoferrate(III);
platinum(IV) oxide; 2,6-di-tert-butyl-4-methyl-phenol;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4039(00)73316-8