Multi-step reaction with 12 steps
1: imidazole, DMAP / dimethylformamide / 15 h / 25 °C
2: tetrahydrofuran / 2 h / -78 °C
3: 75 percent / aq. K2CO3 / tetrahydrofuran / 3 h / 25 °C
4: 96 percent / imidazole / CH2Cl2 / 1 h / 25 °C
5: 94 percent / diethyl ether / 0.17 h / -78 °C
6: AcOH, H2O / tetrahydrofuran / 12 h / 40 °C
7: PPTS / CH2Cl2 / 4 h / 25 °C
8: TBAF / tetrahydrofuran / 2 h / 25 °C
9: Dess-Martin periodinane / CH2Cl2 / 0.42 h / 25 °C
10: CH2Cl2 / 3 h / -78 - -50 °C
11: 95 percent / Et3N, DMAP / CH2Cl2 / 15 h / 25 °C
12: 1.) aq. 0.5 M HCl, 2.) PPTS / 1.) THF, 25 deg C, 6-10 h, 2.) MeOH, 25 deg C, 8 h
With
1H-imidazole; hydrogenchloride; dmap; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; acetic acid; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)79360-9