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Total synthesis of Elenolate, Methyl:
Reference: Kelly. R. C.; Schletter, I. J. Am. Chem. Soc. 1973, 95, 7156. DOI
Keywords: Decarboxylation Oxidative • Electrolysis • Cyclopentadienide+Alkyl-X • Alkyl-X+Na-R • Diels-Alder, Maleic anhydride • Ether-6 • Bicyclo(221) • Alkene → Diol-1,2 • Diol-1,2 → Ketal • Alkene cleavage • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • O-H → O-SO2R • Ketal → Diol-1,2 • Diol-1,2 cleavage • CarboxAcid → CarboxEster •
Reagents: Bromoacetate • OsO4, KClO3 • Electrolysis • Acetone (react) • Permanganate, potassium • Periodate, potassium • Diazomethane • BH4-Na+ • Sulfonyl chloride, methane, Py • Formic acid • Periodate, sodium • Pyridine • Cyclopentadienide • Maleic anhydride •

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