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Total synthesis of Codeine:
Reference: Magnus, P.;Sane, N.; Fauber, B. P.; Lynch, V. J. Am. Chem. Soc. 2009, 131, 16045. DOI
Keywords: Henry reaction • Nitro aldol • Acetal → Aldehyde • Allyl-OH → Allyl-OR • Ether-5 • N-H → N-C(O)OR • Epoxide+Selenolate • Pd/B-Vinyl+Aryl-X • Suzuki coupling • Alkene → Bromohydrin • Phenol C-alkylation • Vinyl-NO2 → Alkyl-NO2 • ConjAdd Nitronate • Nitro → Amine • Enone → Allyl-OH • Reductive amination, B-H • N-H → N-Alkyl • Amine-6 • Epoxide → Allyl-OH • Selenoxide-Ei → Allyl-OR • Bromohydrin → Epoxide • Aryl-Br → Aryl-H • N-C(O)OR → N-Me • EnolEther → acetal • Alkene → Bromohydrin •
Reagents: Pd2(dba)3 • PCy3 • Vinyl-OR • Bromine • MeNO2 • Acetate, ammonium • BH3CN-Na+ • AlH4-Li+ • HCl, H2O • BH3CN-Na+ • O=C(OR)Cl • Bromohydantoin • Hydroxide, potassium • Selenolate, phenyl • Periodate, sodium • AlH4-Li+ • Fluoride, cesium • DMF (solvent) •

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