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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 • CarboxAmide(Weinreb)+Li-R • Reductive amination, B-H • N-H → N-Alkyl • Azomethine ylide Retro-cycloaddition • Retro-1,3-dipolar cycloaddition • Radical reduction(C-Cl) • Birch reduction • Ketone → Enamine • Allylic oxidation → Allyl-OH • Oxidopyridinium • ConjAdd M-CN • EnolTriflate → EneNitrile •
Reagents: Cyanide, AlR2 • Tf2O • AlHiBu2 • Cyanide, zinc • Pd(PPh3)4 • BuLi(tert) • Azide, sodium • Acetyl chloride • BH(OAc)3-Na+ • Acetic acid, trifluoro • PBu3 • BH4-Na+ • SOCl2 • AIBN • AlHiBu2 • PPh3=CH2 • Na°, ROH • HCl, H2O • Pyrrolidine • PPh3=CH2 • SeO2

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