Total synthesis of Cocaine (Pearson):
| Reference: | Mans, D. M.; Pearson, W. H. Org. Lett. 2004, 6, 3305. DOI |
| Reactions: | O-Bn → O-H • Alkyl-OH → Aldehyde • N-Boc → N-H • Cycloaddition Azaallyl anion • Amine-5 • Li/Sn → Li-Azaallyl • Aldol-enamine → Enone (asym) • Amine-6 • Bicyclo(321)-aza • Mitsunobu → Amine • Allyl-OH → Allyl-NR2(2°) • Gabriel synthesis • Alkyl-SR → Alkyl-H • Reductive amination, B-H • Eschweiler-Clarke methylation • Aldehyde → Imine • N-Phthal → N-H • N-H → N-Boc • Pinnick oxidation • Aldehyde → CarboxAcid • CarboxAcid → CarboxEster • O-H → O-C(O)R • Li-SnR3+Aldehyde • |
| Reagents: | SnR3-Li • Imidazole • Hydrazine • SnBu3-CH2-NH2 • BuLi(n) • EneSulfide • Boc2O • Li°/NH3 • RuO4-Pr4N+, NMO • Proline • Chlorite, sodium • Diazomethane • Acetic acid, trifluoro • BH3CN-Na+ • Chiral catalyst (amino-acid) • PPh3, DEAD • Formaldehyde • |