Multi-step reaction with 18 steps
1: 87 percent / imidazole / dimethylformamide / 12 h / 20 °C
2: HgO; HgCl2 / acetone; H2O / 3 h / 60 °C
3: tetrahydrofuran / 3 h / 20 °C
4: 86 percent / HCl / methanol / 3 h / 0 °C
5: 70 percent / p-TsOH / CH2Cl2 / 1 h / -20 - 10 °C
6: CH2Cl2 / 1.58 h / 0 - 20 °C
7: 80 percent / NaN3 / dimethylformamide / 18 h / 60 °C
8: 89 percent / AlCl3; BH3*NMe3 / tetrahydrofuran / 3 h / 0 °C
9: 88 percent / PPh3; DEAD / tetrahydrofuran / 18 h / 20 °C
10: 85 percent / PPh3; H2O / tetrahydrofuran / 4 h / 60 °C
11: 76 percent / NaOH / methanol / 0 - 20 °C
12: 80 percent / Et3N / tetrahydrofuran / 0.03 h / 0 - 20 °C
13: Et3N / CH2Cl2 / 1.58 h / 0 - 20 °C
14: t-BuOK / tetrahydrofuran; CH2Cl2 / 18 h / 20 °C
15: K2OsO4*2H2O; NMO / acetone; H2O / 3 h / 20 °C
16: NaIO4 / diethyl ether; H2O / 2 h / 20 °C
17: 70 percent / tetrahydrofuran / 3 h / 20 °C
18: 90 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / 0 °C
With
1H-imidazole; hydrogenchloride; sodium hydroxide; potassium osmate(VI); sodium periodate; aluminium trichloride; sodium azide; N-methyl-2-indolinone; trimethylamine-borane; potassium tert-butylate; water; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;
3: Grignard addition / 9: Mitsunobu reaction / 10: Staudinger reduction;
DOI:10.1081/CAR-120026470