Multi-step reaction with 15 steps
1: 98 percent / imidazole / dimethylformamide / 0.5 h
2: 98 percent / MgSO4 / benzene / 24 h
3: Ti(O-i-Pr)4; chiral amino acid ligand; isopropanol / toluene / 4 h
4: 3.11 g / NaHCO3; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C
5: NH4OAc; aq. NaIO4 / acetone / 12 h / 22 °C
6: 650 mg / Cu(OAc)2; 4A molecular sieves; Et3N / CH2Cl2; methanol / 6 h / 22 °C
7: 98 percent / HCl / methanol / 1.5 h / 22 °C
8: 860 mg / 2,6-lutidine / CH2Cl2 / 2 h
9: 1.0 g / AlBr3; EtSH / 1.5 h / 0 °C
10: 940 mg / 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; NaHCO3 / tetrahydrofuran / 12 h / 22 °C
11: 390 mg / NIS / acetonitrile / 0.42 h / 22 °C
12: 85 mg / HCl / methanol / 5 h / 45 °C
13: 98 mg / HATU; collidine / tetrahydrofuran; CH2Cl2 / 3 h / 0 - 22 °C
With
1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; hydrogenchloride; sodium periodate; N-iodo-succinimide; 1-hydroxy-7-aza-benzotriazole; aluminum tri-bromide; copper diacetate; 4 A molecular sieve; chiral amino acid ligand; ammonium acetate; sodium hydrogencarbonate; magnesium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; isopropyl alcohol; ethanethiol; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
DOI:10.1021/ja030249r