Total synthesis of Vitamin E (partial):
| Reference: | Cohen, N.; Eichel, W. F.; Lopresti, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3512. DOI |
| Reactions: | Nitrile → Aldehyde • Hydrogenation alkene • Alkyne → Ene-cis (Lindlar) • Mg-Alkyl+Aldehyde • Ynal+Mg-R • Cu-Alkyl+Alkyl-X • Alkyl-X+Cu-R • Mg-R → Cu-R • Alkyl-X → Alkyl-CN • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Alkyne → Ene-trans • Claisen-Johnson • Stereoconvergent • CarboxEster → Alkyl-OH • O-H → O-SO2Ar • |
| Reagents: | Cyanide, sodium • AlHiBu2 • Alkynyl-Li • H2, Pd • Na°/NH3 • AlH4-Li+ • TsCl, Py • H2, RaNi • Alkyl-MgX • Alkyl-MgX • Mg° • Propiolaldehyde • CuCl • Orthoacetate • Orthoacetate • |