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Total synthesis of Cocaine:
Reference: Mans, D. M.; Pearson, W. H. Org. Lett. 2004, 6, 3305. DOI
Keywords: N-Phthal → N-H • N-H → N-Boc • O-Bn → O-H • Alkyl-OH → Aldehyde • Pinnick oxidation • Aldehyde → CarboxAcid • N-Boc → N-H • Cycloaddition Azaallyl anion • Amine-5 • Li/Sn → Li-Azaallyl • Aldol-enamine → Enone(asym) • Mitsunobu → Amine • Allyl-OH → Allyl-NR2(2°) • Gabriel synthesis • Alkyl-SR → Alkyl-H • Reductive amination, B-H • N-H → N-Me •
Reagents: LiSnR3 • Phthalimide • Hydrazine • SnBu3-CH2-NH2 • BuLi(n) • Vinyl-Sulfide • Boc2O • Li°/NH3 • RuO4-Pr4N+, NMO • Proline • Chlorite, sodium • Diazomethane • Benzoyl peroxide • Acetic acid, trifluoro • BH3CN-Na+ • PPh3, DEAD • Formaldehyde •

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