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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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