Multi-step reaction with 15 steps
1.1: 100 percent / imidazole / dimethylformamide / 3 h / 20 °C
2.1: 93 percent / DIBAL / tetrahydrofuran; hexane / 1.5 h / -78 °C
3.1: 87 percent / BF3*Et2O / CH2Cl2; diethyl ether / 2 h / -78 °C
4.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
5.1: 82 percent / NaBH4 / methanol / 0.83 h / -23 °C
6.1: 74 percent / acetic acid; acetic anhydride / 3 h / 40 °C
7.1: 89 percent / LiOH / methanol / 11.5 h / 30 °C
8.1: 91 percent / EDCI*HCl; DMAP / CH2Cl2 / 13 h / 20 °C
9.1: 100 percent / HF*pyridine; pyridine / tetrahydrofuran / 12 h / 40 °C
10.1: 94 percent / EDCI*HCl; DMAP / CH2Cl2 / 2 h / 0 °C
11.1: 97 percent / NH4OAc; Zn powder / tetrahydrofuran / 2 h / 20 °C
12.1: diethylamine / acetonitrile / 2.5 h / 20 °C
13.1: 66 percent / EDCI*HCl; HOAt / CH2Cl2; dimethylformamide / 40.5 h / 20 °C
14.1: 93 percent / 2,6-lutidine; AgNO3 / tetrahydrofuran; H2O / 1 h / 65 °C
15.1: lithium aluminum hydride / diethyl ether / 1.3 h / 20 °C
15.2: 0.05 mg / pyridine / 17 h / 20 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; 1-hydroxy-7-aza-benzotriazole; boron trifluoride diethyl etherate; ammonium acetate; acetic anhydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; zinc;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
3.1: vinylogous Mukaiyama aldol reaction / 4.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2004.06.125