Total synthesis of α-Lycorane:
| Reference: | Wang, C. L.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett., 1984, 25, 4613. DOI |
| Reactions: | Nitrile anion+Alkyl-X • Alkyl-X+Nitrile anion • Nitrile → Aldehyde • CompRed-Nitrile/Alkene+M-H • Pictet-Spengler • Amine-6 • Decarboxylation β-keto acid • Mechanism • Azomethine ylide Cycloaddition • Amine-5 • Bicyclo(430)-aza • N-Bn → N-H • Aldehyde → Imine • |
| Reagents: | LiNiPr2 • AlHiBu2 • NH(SiMe3)2 (HMDS) • Formic acid • Formaldehyde • HMPA (solvent) • |