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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-6(asym) • Mitsunobu -> Amine • Allyl-OH -> Allyl-NR2(2°) • Gabriel synthesis • Alkyl-SR -> Alkyl-H • Reductive amination, B-H •
Reagents: LiSnBu3 • 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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