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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
Keywords: Hydrogenation Lindlar • CarboxEster → Alkyl-OH • O-H → O-SO2R • Nitrile → Aldehyde • Hydrogenation alkene • Hydrogenation Lindlar • Mg-Alkyl+Aldehyde • Ynal+Mg-R • Cu-Alkyl+Alkyl-X • Alkyl-X+Cu-R • Alkyl-X → Alkyl-CN • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Alkyne → Ene-trans • Claisen-Johnson • Stereoconvergent •
Reagents: Cyanide, sodium • AlHiBu2 • Alkynyl-Li • Na°/NH3 • AlH4-Li+ • TsCl, Py • H2, RaNi • Alkyl-MgX • Alkyl-MgX • Mg° • CuCl • Orthoacetate • Orthoacetate •

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