Total synthesis of Ajmalicine (Van Tamelen):
| Reference: | Van Tamelen, E. E.; Placeway, C. J. Am. Chem. Soc. 1961, 83, 2594-2495. DOI |
| Reactions: | Michael EnoateEster • KetoEster enolate+EnoateEster • Mannich • Lactam-6 • Bischler-Napieralski • Amine-6 • Bicyclo(440)-aza • Hydrogenation Enamine • Amine-6 • Decarboxylation β-keto acid • Lactone-6 • Claisen acylation, formate • Aldehyde → Enol-R • Ketone → Alkyl-OH • |
| Reagents: | Acetoacetate • Formaldehyde • POCl3 • H2, Pd • HCl, H2O • BH4-Na+ • Carbodiimide • Formate, ethyl • NaCPh3 • HCl, MeOH • HOMe (react) • |