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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
Keywords: Decarboxylation • Ketone → Alkyl-OH • Lactone-5 • Aryl-Cl → Aryl-H • Claisen acylation, ester • CarboxEster enolate+CarboxEster • Michael EnoateEster • Ketoester enolate+EnoateEster • Decarboxylation • Ketone → CH2 • Hydrogenolysis Ketone • Aryl-H → Aryl-Cl • Friedel-Crafts acylation • Claisen acylation, oxalate • CarboxEster enolate+CarboxEster • Ketone enolate+CarboxEster • Aldol-Mg → Enone • Ketone enolate+Aldehyde • Ketone-α-OR → Ketone • Claisen acylation, acyl-X • CarboxEster enolate+CarboxAnhydride • Claisen acylation, ester • Ketone enolate+CarboxEster • Ketone → Ketone-α-OR • ConjAdd Amine •
Reagents: NaH • Triton B • H2SO4 • Acetic acid • H2, Pd • Acetic acid • Acetic acid • HF • NaH • Oxalate • HCl, H2O • Mg(OMe)2 • Glyoxalate • NHMe2 • BH4-Na+ • TsOH • Zn° • Formic acid • O=C(OR)Cl • NaH • DMF (solvent) • H2, Pd • HBr • O2

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