Multi-step reaction with 12 steps
1: NaIO4, RuCl3 / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
2: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature
3: aq. TFA / 1 h / Ambient temperature
4: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature
5: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature
6: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min.
7: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C
8: DCC, HOBt / dimethylformamide / 68 h / 2 °C
9: 95 percent / SOCl2 / pyridine / 1 h / -30 °C
10: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C
11: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h
12: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C
With
hydrogenchloride; dmap; ruthenium trichloride; sodium periodate; thionyl chloride; hydrogen; oxygen; sodium hydride; benzotriazol-1-ol; ozone; dicyclohexyl-carbodiimide; trifluoroacetic acid;
Raney-Ni W-4;
In
tetrahydrofuran; pyridine; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; Petroleum ether;
DOI:10.1016/S0040-4039(00)70713-1