Total synthesis of Codeine (Magnus):
| Reference: | Magnus, P.;Sane, N.; Fauber, B. P.; Lynch, V. J. Am. Chem. Soc. 2009, 131, 16045. DOI |
| Reactions: | Nitro aldol • Cyclohexene • Bicyclo(440) • Acetal → Aldehyde • Allyl-OH → Allyl-OR • Ether-5 • Selenide → Selenoxide • Pd/B-Aryl+Aryl-X • Alkene → Bromohydrin • Aryl-H → Aryl-Br • Phenol C-alkylation • EneNitro → Alkyl-NO2 • ConjAdd Nitronate • Nitro → Amine • Enone → Allyl-OH • Reductive amination, B-H • Amine-6 • Bicyclo(331)-aza • Ether-5 • Epoxide → Allyl-OH • Selenoxide-Ei → Allyl-OR • Bromohydrin → Epoxide • Epoxidation via halohydrin • Aryl-Br → Aryl-H • N-C(O)OR → N-CH3 • EnolEther → acetal • Alkene → Bromohydrin • N-H → N-C(O)OR • Epoxide+M-SeR • Selenolate+Epoxide • |
| Reagents: | Pd2(dba)3 • PCy3 • Vinyl-OR • Br2 • MeNO2 • Acetate, ammonium • BH3CN-Na+ • AlH4-Li+ • HCl, H2O • BH3CN-Na+ • O=C(OEt)Cl • Bromohydantoin • Hydroxide, potassium • Selenolate, phenyl • Periodate, sodium • AlH4-Li+ • Fluoride, cesium • DMF (solvent) • |