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Total synthesis of Coronofacic Acid:
Reference: Ichihara, A.; Kimura, R.; Yamada, S.; Sakamura, S. J. Am. Chem. Soc. 1980, 102, 6353. DOI
Keywords: Diels-Alder, Intram • Retro-Diels-Alder, cyclopentadiene • Electrocyclic-4π • Ketone epimerization • CarboxEster -> Alkyl-OH • Aldehyde -> Enal • Alkyl-OH -> Aldehyde • O-H -> O-SO2R • Dehydrosulfonoxylation -> Enone • Allyl-OH -> Enal • Jones oxidation • Acetal -> Enal • Enal -> EnoicAcid • ConjReduct Enone • Aldol-Li -> Aldol • Ketone enolate+Aldehyde • Hoffmann elim -> Enoate • Aldehyde enamine+EnoateEster • ConjAdd Enamine • Diels-Alder, Enone •
Reagents: AlH4-Li+ • Glycol • TsOH • CrO3·Py2 (Collins) • Methyl vinyl ketone • LiNiPr2 • MeSO2Cl, NEt3 • DBU • MnO2 • AlH2(OR)2-Na+ • CuI • NaOMe • CrO3, H2SO4 (Jones) • MeOTs •

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