Total synthesis of Ajmalicine (Overman) New:
| Reference: | Loegers, M.; Overman, L. E.; Welmaker, G. S. J. Am. Chem. Soc. 1995, 117, 9139-9150. DOI |
| Reactions: | Enzyme • CarboxCl → CarboxAmide • EnAmine → Amine • N-H → N-SO2R • N-C(O)R → N-CH2R • ConjAdd Cu-Vinyl • Cu-Vinyl+EnoateEster • Mg-R → Cu-R • CarboxAcid → CarboxCl • CarboxCl → Carboxamide • CarboxEster → CarboxAcid • Acyliminium • Cationic cyclization • Lactone-6 • Lactam-6 • Indole synthesis • Aminomethylenation • N-SO2R → N-H • Bischler-Napieralski • Amine-6 • Bicyclo(440)-aza • Iminium → Amine • |
| Reagents: | NEt3 • BH3·THF • Acetic acid, trifluoro • Tf2O • BH3·THF • CuI • SiMe3-Cl • Oxalyl chloride • Hydroxide, lithium • Formaldehyde • Acetic acid, trifluoro • DDQ • Brederick reagent • HCl • HOMe (react) • Carbonate, potassium • POCl3 • BH4-Na+ • |