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Total synthesis of Acanthoic Acid:
Reference: Ling, T.; Chowdhury, C.; Kramer, B. A.; Vong, B. G.; Palladino, M. A.; Theodorakis, E. A. J. Org. Chem. 2001, 66, 8843. DOI
Keywords: Jones oxidation • Allyl-OH -> Enone • Ketone -> Ketal • Luche reduction • Enone -> Allyl-OH • Ketone -> Ketal • O-H -> O-MOM • Dehydration -> Diene • Aldehyde -> Alkyl-OH • Alkyl-OH -> Aldehyde • Robinson annulation, diketone • Ketone enolate+Enone • Barton-McCombie reduction • Allyl-OH -> Allyl-H • Wittig-methyl • EC-Aldehyde/CarboxEster+Wittig • Diels-Alder, Enal • ConjReduct-Acylation Enone • CarboxEster enolate+Enal • ConjReduct-Alkylation EnoateEster • CarboxEster enolate+Alkyl-X • Claisen acylation, Mander • Ketone enolate+Mander • Hydrosulfidation Alkyne • Li-Alkynyl+Ketone • Allyl-SR -> Allyl-H • Mechanism • KetoEster -> Ester •
Reagents: Acrolein • LiNiPr2 • CrO3, H2SO4 (Jones) • Fluoride, potassium • Glycol • BH4-Na+, CeCl3 • CS2 • HSnBu3 • Li°/NH3 • MeI • Glycol • Li°/NH3 • O=C(OR)CN • Cl-CH2-OR • Li°/NH3 • MeI • Alkynyl-Li • HS-Ph • POCl3 • Methacrolein • SnCl4 • BH4-Na+ • RaNi • Dess-Martin • Ph3P=CH2 • Bromide, lithium • AIBN • AIBN • Wieland-Miescher •

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