Total synthesis of Sancycline:
| Reference: | Conover, L. H.; Butler, K.;Johnston, J. D.; Korst, J. J.; Woodward, R. B. J. Am. Chem. Soc. 1962, 84, 3222. DOI |
| Reactions: | CarboxEster → CarboxAcid • Aryl-Cl → Aryl-H • Claisen acylation, ester • CarboxEster enolate+CarboxEster • Michael EnoateEster • KetoEster enolate+EnoateEster • Decarboxylation β-keto acid • Ketone → CH2 • Hydrogenolysis Ketone • Aryl-H → Aryl-Cl • Friedel-Crafts acylation • Cyclohexanone • Claisen acylation, oxalate • CarboxEster enolate+CarboxEster • Aldol-Mg → Enone • Ketone enolate+Aldehyde • Ketone-α-OR → Ketone • Claisen acylation, acyl-X • CarboxEster enolate+Acyl-X • Claisen acylation, ester • Ketone enolate+CarboxEster • Ketone → Ketone-α-OR • ConjAdd Amine • Decarboxylation β-keto acid • Ketone → Alkyl-OH • Lactone-5 • N-But → N-H • Ketone enolate+CarboxEster • Cyclohexanone • Bicyclo(440) • |
| Reagents: | Succinate • NaH • Acrylate • Triton B • H2SO4 • Acetic acid • H2, Pd • Acetic acid • Cl2 • Acetic acid • HF • NaH • Oxalate • HCl, H2O • Mg(OMe)2 • Glyoxalate • NHMe2 • BH4-Na+ • TsOH • Zn° • Formic acid • O=C(OR)Cl • Malonate • NaH • DMF (solvent) • H2, Pd • HBr • O2 • |