Total synthesis of Tetracycline, 6-Demethyl-6-deoxy (Muxfeld):
| Reference: | Muxfeld, H.; Rogalski, W. J. Am. Chem. Soc. 1965, 87, 933-934. DOI |
| Reactions: | Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • Benzyl-X+Enolate • N-But → N-H • O-Me → O-H • Reductive amination, H2 • Eschweiler-Clarke methylation • Friedel-Crafts acylation • Cyclohexanone • Claisen acylation, ester • Ketone enolate+CarboxEster • Cyclohexanone • O-H → O-SO2Me • Aldol-Acid → EnoateEster • Alkyl-X → Alkyl-CN • Cyanide+Alkyl-X • Nitrile → Aldehyde • CarboxEster → CarboxAcid • Ketal → Ketone • CarboxEster → Alkyl-OH • N-C(O)R → N-H • Decarboxylation malonic • CarboxAcid → CarboxEster • Fischer esterification • Ketone → Ketal • |
| Reagents: | Malonate • Succinate • NaOMe • Hydroxide, sodium • Polyphosphoric acid • Acetic anhydride • Pb(OAc)2 • HCl, H2O • Acetoacetate • NaH • Et3O+ X- • Acetic acid • HBr • Formaldehyde • H2, Pd • H2SO4 • Glycol • AlH4-Li+ • Sulfonyl chloride, methane, Py • Cyanide, potassium • AlH(OEt)3-Li+ • HCl, H2O • HOMe (react) • |