Multi-step reaction with 7 steps
1: 80 percent / DMAP / pyridine / 8 h / 110 °C
2: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 15 min; reflux, 24 h
3: 1.) Ph3P)3RhCl, DABCO, 2.) HgCl2, HgO / 1.) PhH, EtOH, H2O, room temperature, 1 h; reflux, 36 h, 2.) me2CO, H2O, room temperature, 12 h
4: 93 percent / LiAlH4 / tetrahydrofuran / 4 h
5: 99 percent / Et3N, DMAP / CH2Cl2 / 16 h
6: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) room temperature, 1 h; reflux, 24 h
7: 92 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature
With
1,4-diaza-bicyclo[2.2.2]octane; dmap; Wilkinson's catalyst; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; mercury dichloride; mercury(II) oxide;
In
tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo990086i