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Total synthesis of Morphine:
Reference: Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028-9. DOI
Keywords: Enolether -> Enone • Enone -> Allyl-OH(asym) • O-H -> O-C(O)NR2 • Diol -> Ketal • Ketal -> 1,2-Diol • Alkene cleavage • O-H -> O-MOM • Li-Aryl -> Aryl-I • Acetal -> Aldehyde • Aldehyde -> Epoxide • Aryl-OH -> Aryl-OR • Aryl-OBn -> Aryl-OH • Epoxide -> Diol • Ether-5 • Alkyl-OH -> Ketone • N-Bn -> N-H • N-H -> N-Alkyl • N-Me -> N-C(O)OR • Selenoxide-Ei -> Enone-6 • N-C(O)OR -> N-Me • Birch alkylation • CarboxAcid enolate+Alkyl-X • Alkene -> Diol-1,2 • Cu-SiR3+Allyl-X • Reductive amination, B-H • Aldehyde -> Acetal(Me) • Li/H -> Li-Aryl • Aldehyde+Sulfonium ylide • Pinacol • Reductive amination, H2 • Epoxidation, peracid • Si-Allyl+Imonium • Imonium+Si-R • Pd-Heck coupling •
Reagents: Li°/NH3 • Allyl-Cl • HCl, H2O • BH(Catechol) • Corey oxazaborolidine • Isocyanate • CuI • BuLi(n) • LiSiMe2Ph • OsO4, NMO • Acetone (react) • TsOH • Periodate, sodium • BH3CN-Na+ • Orthoformate • Cl-CH2-OR • BuLi(n) • I2 • HCl, H2O • Me3S+ I- • BF3·OEt2 • Carbonate, potassium • BF3·OEt2 • Perbenzoic acid, 3,5-dinitro • RuO4-Pr4N+ • H2, Pd • Formaldehyde • O=C(OR)Cl • SePh-Cl • Periodate, sodium • AlH4-Li+ • BBr3 • Pd(OTFA)2(PPh3)2 • Piperidine, pentamethyl •

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