Multi-step reaction with 6 steps
1: 1.) lithium (S,S)-(-)-N,N-bis(1-phenylethyl)amide, LiCl / 1.) THF, hexane, -78 deg C, 120 min, 2.) THF, hexane, -78 deg C, 30 min
2: CeCl3*7H2O, NaBH4 / methanol / 0 - 20 °C
3: 97 percent / Et3N, DMAP / CH2Cl2 / 24 h / Ambient temperature
4: 1.) H2SeO3, Celite, 2.) PDC / 1.) dioxane, H2O, reflux, 18 h, 2.) CH2Cl2, 12 h
5: Zn, aq. EtOH / aq. ethanol / 2 h / Heating
6: 97 percent / H2 / PtO2 / aq. ethanol / 12 h / 2585.7 Torr / Ambient temperature
With
dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; ethanol; Celite; hydrogen; selenious acid; lithium (S,S)-bis(α-methylbenzyl)amide; triethylamine; lithium chloride; zinc;
platinum(IV) oxide;
In
methanol; ethanol; dichloromethane;
DOI:10.1139/v97-091