image

Total synthesis of Cocaine, (S)-(-) (Davis):
Reference: Davis, F. A.; Theddu, N.; Edupuganti, R. Org. Lett. 2010, 12, 4118. DOI
Keywords: N-S(O)R → N-H • CarboxEster enolate+Imine • Imine+Enolate • CarboxEster → Aldehyde • HWE → EnoateEster • Aldehyde → Imine • Imine → Nitrone • Nitrone Cycloaddition • Bicyclo(321) • N-OR → N-H • Sulfinamide, chiral • Amine-5 • O-H → O-C(O)R • Amine → Ammonium • Acetal → Aldehyde •
Reagents: Benzoyl chloride • CH2=C(OLi)(OR) • NaN(SiMe3)2 • AlHiBu2 • P(O)(OR)2CH2-C(O)OR' • DBU • HCl, H2O • H2O2 • ReMeO3 • Al(OtBu)3 • MeOMs • H2, Pd • Pyridine •

Syntheses Home