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Total synthesis of Onocerin:
Reference: Stork, G.; Meisels, A.; Davies, J. E. J. Am. Chem. Soc. 1963, 85, 3419. DOI
Keywords: Dehydration -> Ene • Enolether -> Ketone • Ozonolysis • O-H -> O-C(O)R • Ketone -> Ketal • Mg-Aryl+CarboxEster • CarboxEster+Mg-R • Dehydration -> Ene • Barbier-Wieland degradation • Alkene cleavage • CarboxEster -> CarboxAcid • Birch reduction • Electrolysis • Kolbe • Mg-Alkynyl+Ketone • CarboxEster -> CarboxAcid • Decarboxylation • Mg-Alkyl+Ketone • Pinacol • Robinson annulation, ketone • Ketone enolate+Enone • Enone enolate+Alkyl-X • Deconjugative alkylation • Hydrogenation Alkene • Ynolether -> EnoateEster •
Reagents: MeMgBr • HCl • Methyl vinyl ketone • Hydroxide, potassium • KOtBu • MeI • H2, Pd • Li°/NH3 • HCl, MeOH • H2O2 • Acetic anhydride, Py • Glycol • PhMgBr • Acetic acid • RuO4 • Periodate, sodium • Diazomethane • Alkynyl-MgX • H2SO4 • Hydroxide, potassium • Formic acid •

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