Multi-step reaction with 8 steps
1: 97 percent / zinc triflate / petroleum ether / 1.5 h / Ambient temperature
2: 90 percent / LiAlH4 / tetrahydrofuran / 0.5 h
3: 68 percent / pyridinium dichromate, sodium acetate / CH2Cl2 / 6 h / 0 °C
4: 1.) phenyllithium / 1.) ether, 0 deg C, 2.) 0 deg C, 1 h
5: 1.) 10percent HCl, 2.) concd HCl / diethyl ether / 15 h
6: 89 percent / NaBH4 / methanol / 0.08 h / 0 °C
7: 1.) NaH, 2.) TBAI / 1.) DME, 2a.) room temp. to 80 deg C, 2b.) room temp., 10 h
8: 1.) HgO, BF3*Et2O, 2.) p-toluenesulfonic acid / 1.) THF, H2O, 70 min, 2.) reflux, 4 h
With
hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; boron trifluoride diethyl etherate; sodium acetate; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; phenyllithium; mercury(II) oxide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; Petroleum ether;
DOI:10.1021/jo00277a017