image

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 • Barton-McCombie reduction • Allyl-OR → Allyl-H • Wittig-methyl • CompE+-Aldehyde/CarboxEster+Wittig • ConjReduct-Acylation • Enone ConjReduct • CarboxEster enolate+Enal • Enal+Enolate • ConjReduct-Alkylation • CarboxEster enolate+Alkyl-X • EnoateEster ConjReduct • Alkyl-X+Enolate • Claisen acylation, Mander • Ketone enolate+Mander • Hydrosulfidation Alkyne • Li-Alkynyl+Ketone • Li/H → Li-Alkynyl • Allyl-X → Allyl-H • Mechanism • KetoEster → Ester • Diels-Alder, Enal • Robinson annulation, diketone • Ketone enolate+Enone •
Reagents: Acrolein • LiNiPr2 • CrO3, H2SO4 (Jones) • Glycol • BH4-Na+, CeCl3 • CS2 • HSnBu3 • Li°/NH3 • MeI • Glycol • Li°/NH3 • O=C(OR)CN • Cl-CH2-OR • Li°/NH3 • MeI • Alkynyl-Li • Thiol, phenyl • POCl3 • BH4-Na+ • RaNi • Dess-Martin • PPh3=CH2 • Bromide, lithium • AIBN • AIBN • Wieland-Miescher • Methacrolein • SnCl4 • Fluoride, potassium •

Syntheses Home