Total synthesis of Porantherine:
| Reference: | Corey, E. J.; Balanso, R. D. J. Am. Chem. Soc. 1974, 96, 6516–6517. DOI |
| Reactions: | Ketal → Ketone • Mg-Alkyl+CarboxEster • CarboxEster+Mg-R • Alkyl-OH → Ketone • Ketone → Imine • Li-Alkyl+Imine • Imine+M-R • Ketone → Imine • Amine-6 • Mannich • Bicyclo(331)-aza • Amine-6 • N-Me → N-C(O)OR • Alkene cleavage • Lemieux-Johnson oxidation • Ketone → Ketal • Aldehyde → Acetal • Aldehyde → EnAmine • Bicyclo(440)-aza • Mannich • Bicyclo(440)-aza • Ketone → Alkyl-OH • Amine-6 • Ketal → Ketone • |
| Reagents: | Formate, ethyl • Alkyl-MgX • CrO3·Py2 (Collins) • NH2Me • Alkyl-Li • HCl, H2O • Propenyl-OR • TsOH • CrO3·Py2 (Collins) • OsO4, NaIO4 • Glycol • HCl, H2O • TsOH • BH4-Na+ • SOCl2 • |