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