image

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

Syntheses Home