image

Total synthesis of Tetracycline, 6-demethyl-6-deoxy New:
Reference: Muxfeld, H.; Rogalski, W. J. Am. Chem. Soc. 1965, 87, 933-934. DOI
Keywords: CarboxEster -> CarboxAcid • Decarboxylation • Ketal -> Ketone • N-C(O)R -> N-H • Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • N-tBu -> N-H • O-Me -> O-H • Reductive amination, H2 • Friedel-Crafts acylation • Claisen acylation, acyl-X • Ketone enolate+CarboxEster • CarboxAcid -> CarboxEster • Ketone -> Ketal • CarboxEster -> Alkyl-OH • O-H -> O-SO2R • Aldol-H+ • Alkyl-X -> Alkyl-CN • Nitrile -> Aldehyde •
Reagents: NaOMe • Hydroxide, sodium • Polyphosphoric acid • Acetic anhydride • Pb(OAc)2 • HCl, H2O • NaH • Et3O+ X- • Acetic acid • HBr • Formaldehyde • H2, Pd • H2SO4 • Glycol • AlH4-Li+ • MeSO2Cl • Cyanide, potassium • AlH(OEt)3-Li+ • HCl, H2O •

Syntheses Home