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Total synthesis of Nominine:
Reference: Peese, K. M.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 8734. DOI
Keywords: Nitrile -> Aldehyde • Li/H -> Li-Aryl • Alkyl-X -> Alkyl-N3 • Ketone -> Ketal • Azide -> Amine • Ketone -> Alkyl-OH • Alkyl-OH -> Alkyl-Cl • Nitrile -> Aldehyde • Wittig-Methyl • Enolether -> Ketone • Diels-Alder, Intram • Wittig-Methyl • Azomethine ylide Cycloaddition • Amine-5 • Li-Aryl+CarboxAmide(Weinreb) • CarboxAmide(Weinreb)+Li-R • Reductive amination, B-H • N-H -> N-Alkyl • Azomethine ylide Retro-cycloaddition • Radical reduction(C-Cl) • Birch reduction • Ketone -> Enamine • Allylic oxidation -> Allyl-OH • Oxidopyridinium • ConjAdd M-CN • Vinyl-OTf -> EneNitrile •
Reagents: AlEt2-CN • Tf2O • Cyanide, zinc • Pd(PPh3)4 • BuLi(tert) • Azide, sodium • Acetyl chloride • BH(OAc)3-Na+ • PBu3 • BH4-Na+ • SOCl2 • AIBN • PPh3=CH2 • Na° • HCl, H2O • Pyrrolidine • PPh3=CH2 • SeO2

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