Multi-step reaction with 13 steps
1.1: 50 percent / LiClO4 / Electrochemical reaction
2.1: 70 percent / Zn; AcOH / tetrahydrofuran / 0 °C
3.1: 100 percent / DIPEA / CH2Cl2
4.1: 100 percent / K2CO3; MeOH / 20 °C
5.1: 100 percent / imidazole / dimethylformamide / 6 h
6.1: n-BuLi / tetrahydrofuran; hexane / 0.05 h / -78 °C
6.2: B(OMe)3 / tetrahydrofuran; hexane / 2 h
6.3: 64 percent / H2O2; NaOH / tetrahydrofuran; hexane; H2O / 0 °C
7.1: 100 percent / K2CO3 / dimethylformamide
8.1: 84 percent / HCO2NH4 / Pd/C / ethanol / 3 h / 60 °C
9.1: 100 percent / TBAF / tetrahydrofuran
10.1: 81 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 2 h / 20 °C
11.1: 52 percent / PDC / dimethylformamide / 20 °C
12.1: 96 percent / Et3N; HOBt; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH2Cl2 / 20 °C
13.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
13.2: 67 percent / tetrahydrofuran; hexane / 0.5 h
With
pyridine; 1H-imidazole; methanol; dipyridinium dichromate; n-butyllithium; tetrabutyl ammonium fluoride; ammonium formate; lithium perchlorate; potassium carbonate; benzotriazol-1-ol; Dess-Martin periodane; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; zinc;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2005.11.055