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Total synthesis of Triquinacene:
Reference: Woodward, R. B.; Fukanage, T.; Kelly, R. C. J. Am. Chem. Soc. 1964, 86, 3162-3164. DOI
Keywords: CarboxAcid → CarboxEster • CarboxAnhydride → CarboxAcid • CarboxEster → CarboxAcid • CarboxAcid → CarboxCl • Cope elimination • Alkyl-OH → Ketone • Epoxidation, peracid • Curtius • C-CO2H → C-N • CarboxCl → CarboxAzide • CarboxAcid → CarboxCl • Alkyl-OH → Ketone • N-C(O)OR → N-Me • Leuckart • Reductive amination, HCO2H • Ketone enolate+Epoxide • Epoxide+Enolate • CarboxEster epimerization •
Reagents: CrO3·Py2 (Collins) • Peracetic acid • CrO3, H2SO4 (Jones) • Pb(OAc)4 • Diazomethane • NaOMe • Hydroxide, sodium • SOCl2 • Azide, sodium • AlH4-Li+ • Formaldehyde • Formic acid • H2O2 • KOtBu •

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