Total synthesis of Vincamine:
| Reference: | Herrmann, J. L.; Cregge,R. J.; Richman, J. E.; Semmelhack, C. L.; Schlessinger, R. H. J. Am. Chem. Soc., 1974, 96, 3702–3703. DOI |
| Reactions: | Aminal • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • CarboxCl → CarboxAmide • N-H → N-Alkyl • ConjAdd Enolate • CarboxAmide enolate+EnoateEster • Bischler-Napieralski • Bicyclo(440)-aza • Iminium → Amine • Amine-6 • CarboxEster → CarboxAmide • Pummerer • Lactam-6 • CarboxEster epimerization • CarboxAcid → CarboxCl • Sulfide → Sulfoxide • |
| Reagents: | LiNiPr2 • HMPA (solvent) • TsOH • Oxalyl chloride • KH • LiNiPr2 • Acrylate • POCl3 • AlH(OtBu)3-Li+ • NaH • Acetyl chloride • NaOMe • NaOMe • Perbenzoic acid, 3-chloro • |