image

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 • Kolbe electrolysis • Electrolysis • Mg-Alkynyl+Ketone • CarboxEster → CarboxAcid • Decarboxylation • Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Pinacol • Robinson annulation, ketone • Ketone enolate+Enone • Enone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • Hydrogenation alkene • Ynolether → EnoateEster • Alkene → Diol-1,2 •
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 • Electrolysis •

Syntheses Home