Total synthesis of Phenserine (Rigby):
| Reference: | Rigby, J. H.; Sidique, S. Org. Lett. 2007, 9, 1219 DOI |
| Reactions: | Carbene Cycloaddition • Carbene, bisphenylthio • Lactam-5 • Curtius • C-CO2H → C-N • 1,1-Dipolarophile • Retro-1,3-dipolar cycloaddition • N-C(O)R → N-CH2R • N-H → N-Me • Fischer Indole • Indole synthesis • CarboxAcid → CarboxAzide • Ketal(thio) → CH2 • Imine → Amine • Bicyclo(330)-aza • O-Me → O-H (phenol) • O-H → O-C(O)NR2 • Japp-Klingemann • Diazotization • N-H → N-Me • CarboxEster → CarboxAcid • |
| Reagents: | Nitrite, sodium • Hydroxide, potassium • Acetoacetate • HCl, EtOH • MeI • Hydroxide, lithium • Azide, diphenylphosphoryl • AlH4-Li+ • MeI • RaNi • AlH4-Li+ • B(Br)3 • Isocyanate • DMF (solvent) • |