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Total synthesis of Uleine:
Reference: Buchi, G.; Gould, S. J.; Naf, F. J. Am. Chem. Soc. 1971, 93, 2492. DOI
Keywords: Mechanism • Aldehyde → Imine • Mechanism • Mannich • Amine-6 • Gabriel synthesis • N-H → N-Alkyl • N-H → N-C(O)H • Alkyne → Ketone • Ester Pyrolysis • Enone → Ketone • Hydrogenation Enone • Pictet-Spengler • Indole synthesis • N-CHO → N-Me • Ketone-α-OR → Ketone • Pictet-Spengler • Indole synthesis • Li-Alkynyl+Ketone • CompE+-Ketone/CarboxAmide+M-R • N-CHO → N-Me •
Reagents: Imidazole • HCl, H2O • Formic acetic anhydride • Alkynyl-K • Hg(OAc)2 • Flash vacuum pyrolysis • H2, Pd • BF3·OEt2 • AlH4-Li+ • Li°/NH3 • BF3·OEt2 • AlH4-Li+ • Hydroxide, sodium • Alkynyl-K •

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