Multi-step reaction with 9 steps
1: 84 percent / LAH, NaOMe / tetrahydrofuran / 1 h / Heating
2: 70 percent / tert-butyl hydroperoxide, 3 A molecular sieve, L-(+)-diisopropyl tartrate, tetraisopropyl orthotitanate / CH2Cl2; 2,2,4-trimethyl-pentane / 4 h / -20 °C
3: 76 percent / RuO2, NaIO4 / acetonitrile; CCl4; H2O / 4 h / 30 °C
4: 1.) aq. KHCO3, 2.) aq. conc. NH4OH / 1.) MeOH, 2.) 50 deg C, 20 h
5: dioxane; H2O / 3 h
6: 51 percent / aq. 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 4 h
7: 50 percent / diisopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 2 h / Ambient temperature
8: 87 percent / p-TsOH, EtOH / 2 h / 80 °C
9: 99 percent / Et3N / CH2Cl2 / 1 h / Ambient temperature
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium(IV) oxide; ammonium hydroxide; sodium periodate; lithium aluminium tetrahydride; ethanol; L-(+)-diisopropyl tartrate; di-isopropyl azodicarboxylate; 3 A molecular sieve; sodium methylate; potassium hydrogencarbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; 2,2,4-trimethylpentane; dichloromethane; water; acetonitrile;
DOI:10.1021/jm9800245