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Total synthesis of Codeine (Gates):
Reference: Gates, M.; Tschudi, G. J. Am. Chem. Soc., 1956, 78, 1380 DOI
Keywords: Aryl-H → Aryl-N=O • Quinone synthesis • O-H → O-C(O)R (phenol) • Aryl-N=O → Aryl-NH2 • Quinone synthesis • Michael Enone • ConjAdd Enolate • Decarboxylation malonic • Quinone → Hydroquinone • O-H → O-Alkyl (phenol) • O-C(O)R → O-H (phenol) • Aryl-H → Aryl-N=O • Aryl-N=O → Aryl-NH2 • Quinone synthesis • Quinone synthesis • Wolff-Kishner • Ketone → CH2 • N-H → N-Me • Diels-Alder, Enone • Reductive amination, H2 • Lactam-6 • Oppenauer oxidation • Alkyl-OH → Ketone • CarboxAmide → Amine • Amine-6 • Alkene hydration • O-Me → O-H (phenol) • Ketone epimerization • Ketone → Ketone-α-Halo • Ketone → Enone • Hydrogenation Enone • Aryl-H → Aryl-Br • Ketone → Ketone-α-Halo • O-Me → O-H (phenol) • Ketone → Enone • Ketone → Ketone-α-OR • Enone → Allyl-OH • Aryl-Br → Aryl-H •
Reagents: Benzoyl chloride • Nitrite, sodium • H2, Pd • FeCl3 • SO2 • Sulfate, dimethyl • Hydroxide, potassium • Nitrite, sodium • H2, Pd • FeCl3 • Malonate • NEt3 • Fe(CN)6K3 • Hydroxide, potassium • CuO • Hydrazine • MeI • Butadiene • AlH4-Li+ • H2SO4 • KOtBu • Br2 • Hydrazine, phenyl • HCl, H2O • H2, Pt • Br2 • Hydrazine, phenyl • HCl, H2O • AlH4-Li+

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