Multi-step reaction with 13 steps
1: 97 percent / Et3N / CH2Cl2 / 2 h / -78 °C
2: 1.) NaN3, 2.) aq. NH4OH / 1.) EtOH, H2O, 80 deg C, 3 h, 2.) CH3OH, 12 h
3: 88 percent / Bu4NBr, aq. NaOH / 5 h / 60 °C
4: 98 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1 h
5: 79 percent / Dess-Martin reagent / CH2Cl2 / 1 h
6: 91 percent / NaClO2, NaH2PO4, 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 0.5 h
7: 94 percent / 1-hydroxybenzotriazole, Et3N, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 18 h
8: H2 / Pd(OH)2/C / methanol / 1 h
9: CH2Cl2 / 12 h
10: 97 percent / I2, NaHCO3 / methanol; H2O / 0.5 h
11: 1.) C6H5SH, CF3COOH / 1.) 1 h, 2.) CH2Cl2, 6 h
12: 73 percent / aq. NaOH / methanol / 3 h
13: 1.) p-nitrophenol, dicyclohexylcarbodiimide / 1.) THF, 2.) THF
With
ammonium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; sodium azide; 4-nitro-phenol; 2-methyl-but-2-ene; tetrabutylammomium bromide; hydrogen; iodine; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; thiophenol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium dihydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0968-0896(99)00054-1