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Total synthesis of Pumiliotoxin C:
Reference: LeBel, N. A.; Balasubramanian, N J. Am. Chem. Soc. 1989, 111, 3363. DOI
Keywords: Reductive amination, B-H • N-OR → N-H • N-H → N-Boc • O-H → O-SO2R • Ketone azaenolate+Alkyl-X • Alkyl-X+Azaenolate • Imine → Ketone • Ketone → Oxime • Nitrone synthesis • Aldehyde → Nitrone • Nitrone Cycloaddition • Amine-6 • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Alkyl-SO2R → Alkyl-H • N-Boc → N-H •
Reagents: BuLi(n) • Periodate, sodium • NH2OH • BH3CN-Na+ • Zn° • Boc2O • TsCl, Py • BuLi(n) • HMPA (solvent) • Na(Hg) • Acetic acid, trifluoro •

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