Multi-step reaction with 10 steps
1: 80 percent / BF3*Et2O / 95 °C
2: 70 percent / p-TsOH / acetonitrile / 0 °C
3: 88 percent / CF3SO3H / tetrahydrofuran; diethyl ether / 0 °C
4: HCO2H, Et3N / Pd(PPh3)4 / dioxane / 65 - 95 °C
5: AcOH / Ambient temperature
6: 70 percent / In, TBAI, H2O, HCl / acetonitrile / 40 °C
7: 91 percent / (i-Pr)2NEt, TBAI, 4-pyrrolidinylpyridine / 1,2-dichloro-ethane / 0 - 25 °C
8: 92 percent / DDQ, H2O / CH2Cl2 / Ambient temperature
9: 98 percent / Dess-Martin periodinane / CH2Cl2 / Ambient temperature
10: SmI2, tert-BuOH / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature
With
hydrogenchloride; indium; formic acid; samarium diiodide; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; water; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1002/(SICI)1521-3773(19980703)37:12<1732::AID-ANIE1732>3.0.CO;2-I