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Total synthesis of Codeine New:
Reference: Gates, M.; Tschudi, G. J. Am. Chem. Soc., 1956, 78, 1380 DOI
Keywords: O-H -> O-C(O)R • Ar-N=O -> Ar-NH2 • Aryl-H -> Aryl-N=O • Ar-N=O -> Ar-NH2 • Wolff-Kishner • Oppenauer oxidation • Ketone -> Enone • Ketone epimerization • Hydrogenation Enone • Aryl-OMe -> Aryl-OH • Quinoline synthesis • Michael Enone • ConjAdd Enolate • Decarboxylation • Diels-Alder, Enone • Reductive amination, H2 • CarboxAmide -> Amine • Alkene hydration • Ketone -> Ketone-α-Br • Ketone -> Enone • Ketone -> Ketone-α-OR • Enone -> Allyl-OH • Aryl-Br -> Aryl-H •
Reagents: Benzoyl chloride • Nitrite, sodium • H2, Pd • FeCl3 • SO2 • Me2SO4 • Hydroxide, potassium • Nitrite, sodium • H2, Pd • FeCl3 • NEt3 • Fe(CN)6K3 • Hydroxide, potassium • CuO • Hydrazine • MeI • AlH4-Li+ • H2SO4 • KOtBu • Bromine • HCl • H2, Pt • Bromine • HCl • AlH4-Li+

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