Multi-step reaction with 10 steps
1: 1.) tBuLi / 1.) ether, -78 deg C, 2.) ether, THF, from -78 deg C to 0 deg C
2: H2, AcOH / 20percent Pd(OH)2-C / 760 Torr
3: DMAP, pyridine / 25 °C
4: CrO3, H2SO4 / acetone / 0 - 25 °C
5: aq. NaOH / tetrahydrofuran / 25 °C
6: HCl / 0 °C
7: CrO3, H2SO4 / acetone / 25 °C
8: 1-hydroxybenzotriazole, Et3N, ethyl (3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 0 - 25 °C
9: (iPr)2NEt / CH2Cl2 / 0 °C
10: K2CO3 / acetone / 65 °C
With
pyridine; chromium(VI) oxide; hydrogenchloride; dmap; sodium hydroxide; sulfuric acid; hydrogen; tert.-butyl lithium; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine;
palladium hydroxide - carbon;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00062a013