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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 • Electrocyclic-4π • Ketone epimerization • CarboxEster → Alkyl-OH • Aldehyde → Enal • Alkyl-OH → Aldehyde • O-H → O-SO2R • Dehydrosulfonoxylation → Enone • Allyl-OH → Enal • Retro-Diels-Alder → Alkene • Jones oxidation • Acetal → Enal • Enal → EnoateAcid • ConjReduct Enone • Aldol-Li → Aldol • Ketone enolate+Aldehyde • Hofmann elim → Enoate • Aldehyde enamine+EnoateEster • ConjAdd Enamine • Diels-Alder, Enone • CompOx-Allyl-OH/Alkyl-OH+MnO2 •
Reagents: AlH4-Li+ • Glycol • TsOH • CrO3·Py2 (Collins) • Methyl vinyl ketone • LiNiPr2 • Sulfonyl chloride, methane, NEt3 • DBU • MnO2 • AlH2(OR)2-Na+ • CuI • NaOMe • CrO3, H2SO4 (Jones) • MeOTs •

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