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Total synthesis of Cocaine:
Reference: Mans, D. M.; Pearson, W. H. Org. Lett. 2004, 6, 3305
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 --- CF3CO2H --- BH3CN-Na+ --- PPh3, DEAD --- Formaldehyde

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