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Total synthesis of Tetracycline, 6-Demethyl-6-deoxy:
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 • Alkyl-X+Enolate • N-But → N-H • O-Me → O-H • Reductive amination, H2 • Friedel-Crafts acylation • Claisen acylation, ester • Ketone enolate+CarboxEster • CarboxAcid → CarboxEster • Fischer esterification • Ketone → Ketal • CarboxEster → Alkyl-OH • O-H → O-SO2R • Aldol-H+ → EnoateEster • 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+ • Sulfonyl chloride, methane • Cyanide, potassium • AlH(OEt)3-Li+ • HCl, H2O •

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