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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: EnolEther → Ketone • Barbier-Wieland degradation • Alkene cleavage • Birch reduction • Kolbe electrolysis • Electrolysis • Radical coupling • Mg-Alkynyl+Ketone • CompE+-Ketone/CarboxEster+M-R • Decarboxylation • Robinson annulation, ketone • Ketone enolate+Enone • Cyclohexenone • Enone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • Hydrogenation alkene • Ynolether → EnoateEster • O-H → O-C(O)R • Ozonolysis • Decarboxylation Oxidative • Mg-Aryl+CarboxEster • CarboxEster+Mg-R • CarboxEster → CarboxAcid • Ketone → Ketal • CarboxEster → CarboxAcid • Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Pinacol • Alkene → Diol-1,2 • Dehydration → Ene • Dehydration → Ene •
Reagents: Methyl vinyl ketone • Hydroxide, potassium • KOtBu • MeI • H2, Pd • Li°/NH3 • HCl, MeOH • O3 • H2O2 • Acetic anhydride, Py • Glycol • Aryl-MgX • Acetic acid • RuO4 • Periodate, sodium • Diazomethane • H2SO4 • Hydroxide, potassium • Formic acid • Electrolysis • Alkynyl-MgX • MeMgBr • HCl •

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