Total synthesis of Elenolate, Methyl:
| Reference: | Kelly. R. C.; Schletter, I. J. Am. Chem. Soc. 1973, 95, 7156. DOI |
| Reactions: | 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-SO2Me • 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 • |