Multi-step reaction with 9 steps
1: CrO3, pyridine, Ac2O / CH2Cl2 / 0.33 h
2: diethyl ether / 0.33 h
3: 1.) NaH / 1.) THF, 30 min, 2.) 1 h
4: 87 percent / Bu3SnH, AIBN / toluene / 2.5 h / Heating
5: 84 percent / HCl / tetrahydrofuran
6: 1.) NaH, 2.) Bu4NI / 1.) THF, room temperature, 1 h, 2.) 2 d
7: 0.88 g / CdCO3, HgCl2 / acetone; H2O / 4 h / Ambient temperature
8: pyridinium dichromate / dimethylformamide / 16 h / Ambient temperature
9: 1.) HOBT, DCC / 1.) CH2Cl2, 2 h, 2.) CH2Cl2, room temperature, 3 d
With
pyridine; chromium(VI) oxide; hydrogenchloride; dipyridinium dichromate; cadmium(II) carbonate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; mercury dichloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4020(97)00877-6