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Total synthesis of Pupukeanone, 9-Isocyano- (Corey):
Reference: Corey, E. J.; Behforouz, M.; Ishiguro, M. J. Am. Chem. Soc. 1979, 101, 1608. DOI
Keywords: Lactone-6 • Friedel-Crafts Acylation • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Hydrogenation Benzene • Lactone-6 • Li-Isocyanide • Nitrile → CarboxEster • Cu-Alkyl+EnoateEster • ConjAdd Cu-R • EnoateEster+Cu-R • Amine → Isocyanide • Baldwin rules • Reductive cyanation • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Cyclohexanone • Ketone → Oxime • CarboxAcid → CarboxEster • O-Me → O-H (phenol) • CarboxEster → Alkyl-OH • O-H → O-SO2R • Alkyl-OH → Ketone • Reductive amination, H2 • N-H → N-Alkyl •
Reagents: Alkyl-MgX • CuSPh • KOtBu • H2O2, KOH • Diazomethane • LiNiPr2 • MeI • B(Br)3 • H2, cat • AlH4-Li+ • TsCl, Py • CrO3Cl·PyH (PCC) • NH2OH • H2, cat • Sulfonyl chloride, methane, Py • Polyphosphoric acid • TsCH2NC • HMPA (solvent) • KOtBu • HMPA (solvent) • Formic acetic anhydride •

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