Total synthesis of Uleine:
| Reference: | Buchi, G.; Gould, S. J.; Naf, F. J. Am. Chem. Soc. 1971, 93, 2492. DOI |
| Reactions: | 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 • Bicyclo(331)-aza • N-C(O)H → N-CH3 • Ketone-α-OR → Ketone • Pictet-Spengler • Indole synthesis • Li-Alkynyl+Ketone • CompE+-Ketone/CarboxAmide+M-R • N-C(O)H → N-CH3 • |
| 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 • |